Tandem diazotization/cyclization approach for the synthesis of a fused 1,2,3-triazinone-furazan/furoxan heterocyclic system

• Yuri A. Sidunets,
• Valeriya G. Melekhina and
• Leonid L. Fershtat

Beilstein J. Org. Chem. 2024, 20, 2342–2348, doi:10.3762/bjoc.20.200

• a 1,2,3-triazin-4-one core. The proposed method is based on tandem diazotization/azo coupling reactions of the corresponding amides (Scheme 1). In addition, application perspectives of thus prepared heterocyclic entities as thermally stable components of functional organic materials or NO-donor drug

• extended this approach to amides 5 containing a furazan ring that were obtained via the reaction of readily available 4-amino-3-furazancarboxylic acid 6 with various amines using 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethylaminium tetrafluoroborate (TBTU) as a coupling reagent (Scheme 3; see Supporting

• Information File 1 for details) [43]. As expected, amides 5 also undergo tandem diazotization/azo coupling reaction to form the target [1,2,5]oxadiazolo[3,4-d][1,2,3]triazin-7(6H)-ones 7. It should also be noted, that compounds 7 were obtained in similar yields as the corresponding furoxan analogues

Deuterated reagents in multicomponent reactions to afford deuterium-labeled products

• Kevin Schofield,
• Shayna Maddern,
• Yueteng Zhang,
• Grace E. Mastin,
• Rachel Knight,
• Wei Wang,
• James Galligan and
• Christopher Hulme

Beilstein J. Org. Chem. 2024, 20, 2270–2279, doi:10.3762/bjoc.20.195

• is comprised of reaction of an isonitrile, amine, and aldehyde/ketone, in the presence of phenylphosphinic acid (PPA), to give α-amino amides [35]. Examples of deuterated Ugi-3CR products are represented in Scheme 4. Like the Ugi 4-CR reaction, there was no deuterium scrambling in the Ugi 3-CR. Using

• the Passerini reaction [40][41][42][43] discovered 60 years prior to the Ugi reaction. It uses the reactivity of isocyanides, aldehydes, and carboxylic acids to yield α-acyloxy amides (Scheme 6). Six deuterated analogs are reported in good yield with no observation of deuterium scrambling. For the

Selective hydrolysis of α-oxo ketene N,S-acetals in water: switchable aqueous synthesis of β-keto thioesters and β-keto amides

• Haifeng Yu,
• Wanting Zhang,
• Xuejing Cui,
• Zida Liu,
• Xifu Zhang and
• Xiaobo Zhao

Beilstein J. Org. Chem. 2024, 20, 2225–2233, doi:10.3762/bjoc.20.190

• thioesters and β-keto amides is reported. In refluxing water, the hydrolysis reactions of α-oxo ketene N,S-acetals in the presence of 1.0 equiv of dodecylbenzenesulfonic acid effectively afforded β-keto thioesters in excellent yield, while β-keto amides were successfully obtained in excellent yield when the

• hydrolysis reactions were carried out in the presence of 3.0 equiv of NaOH. The green approach to β-keto thioesters and β-keto amides avoids the use of harmful organic solvents, thiols and thiolacetates as well as amines, which could result in serious environmental and safety issues. Keywords: α-oxo ketene

• structural characters and multiple good reactivities [1][2][3][4]. Both β-keto thioesters [5][6][7][8][9][10][11][12] and β-keto amides [13][14][15][16][17][18][19][20][21][22] have served as useful synthetic intermediates for the synthesis of a range of potent natural products. Therefore, much effort has

O,S,Se-containing Biginelli products based on cyclic β-ketosulfone and their postfunctionalization

• Kateryna V. Dil and
• Vitalii A. Palchykov

Beilstein J. Org. Chem. 2024, 20, 2143–2151, doi:10.3762/bjoc.20.184

• amides, coumarins, alicyclic ketones, β-ketophosphonates, α-nitroketones, curcumin, and barbituric acid derivatives [1][2][8][9]. We analyzed a number of Biginelli-type products and publications and concluded that Se-containing DHPMs among the rarest examples and, in addition to this, ketosulfones have

Access to 2-oxoazetidine-3-carboxylic acid derivatives via thermal microwave-assisted Wolff rearrangement of 3-diazotetramic acids in the presence of nucleophiles

• Ivan Lyutin,
• Vasilisa Krivovicheva,
• Grigory Kantin and
• Dmitry Dar’in

Beilstein J. Org. Chem. 2024, 20, 1894–1899, doi:10.3762/bjoc.20.164

• well as a wide range of nucleophiles provides access to a structural diversity of medically relevant 2-oxoazetidine-3-carboxylic acid amides and esters. Keywords: β-lactams; diazotetramic acids; nucleophiles; spirocycles; thermolysis; Wolff rearrangement; Introduction The importance of the β-lactam

• derivatives (mainly amides) exhibit various types of biological activity, among which the following can be highlighted: inhibition of β-lactamases [4][5], antitubercular properties [6], antiproliferative and antibacterial activity [7], herbicidal properties [8][9], inhibition of neutral amino acid transporter

• (SLC6A19) [10]. Hence, developing new synthetic methods to create structurally diverse 2-oxoazetidine-3-carboxylic acid derivatives is a highly valuable endeavour that could have a positive impact on future drug discovery. Most synthetic approaches to amides and esters of 2-oxoazetidine-3-carboxylic acids

Oxidative fluorination with Selectfluor: A convenient procedure for preparing hypervalent iodine(V) fluorides

• Samuel M. G. Dearman,
• Xiang Li,
• Yang Li,
• Kuldip Singh and
• Alison M. Stuart

Beilstein J. Org. Chem. 2024, 20, 1785–1793, doi:10.3762/bjoc.20.157

• ring to stabilise the iodine(V) centre. Both sidearms were also changed to amides because the NR group is a point of diversity which could be used to modulate the sterics and electronics of these novel hypervalent iodine(V) compounds. Initially, we applied Togni’s oxidative fluorination protocol to

• be the best reagent for preparing bicyclic iodine(V) difluoride 6, this route was first investigated for the oxidative fluorinations of hypervalent iodine(III) amides 11a and 11b (Scheme 3). Unfortunately, these reactions did not work and difluoro(aryl)-λ5-iodanes 7a and 7b were not produced. Togni’s

• protocol using TCCA (4 equivalents) and KF (6 equivalents) was then applied to both bicyclic iodine(III) amides 11a and 11b, but these reactions also failed to form either difluoroiodane 7a or 7b. Following the successful preparation and isolation of difluoroiodane 6, we investigated its ability to

Ugi bisamides based on pyrrolyl-β-chlorovinylaldehyde and their unusual transformations

• Alexander V. Tsygankov,
• Vladyslav O. Vereshchak,
• Tetiana O. Savluk,
• Serhiy M. Desenko,
• Valeriia V. Ananieva,
• Oleksandr V. Buravov,
• Yana I. Sakhno,
• Svitlana V. Shishkina and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2024, 20, 1773–1784, doi:10.3762/bjoc.20.156

• prepared and characterized. Surprisingly, a well-documented approach to obtain peptide-containing carboxylic acids through acid hydrolysis of the convertible isocyanide moiety in the Ugi bisamides proceeded in an unexpected manner in our case, leading to the formation of derivatives of amides of

• the double bond are trans configured. To find out the patterns of the new reaction, we applied different conditions to a wider range of starting bisamides 5–8 (Table 2). As in the model reaction (Scheme 3), the main products of the transformation were the corresponding amides 10a–d (Table 2). In the

• of p-CF3-substituted aniline when synthesizing bisamide 6d. The yield of the amide 10c was about 8% and it was also the first to precipitate. In addition, it is worth mentioning that the corresponding amides 10 were observed in 1H NMR spectra and LC–MS analysis in many mother liquors after filtration

Syntheses and medicinal chemistry of spiro heterocyclic steroids

• Laura L. Romero-Hernández,
• Ana Isabel Ahuja-Casarín,
• Penélope Merino-Montiel,
• Sara Montiel-Smith,
• José Luis Vega-Báez and
• Jesús Sandoval-Ramírez

Beilstein J. Org. Chem. 2024, 20, 1713–1745, doi:10.3762/bjoc.20.152

• ester under basic conditions was carried out, followed by the transformation of the carboxyl group to the amides 165 and 166 by treatment with thionyl chloride and the corresponding amine. Tetraoxanes were obtained from ketones 163, 165, and 166 by a peroxyacylation reaction using an acidic hydrogen

• on normal human peripheral blood mononuclear cells (PBMC). In 2003, a direct transformation of tetraoxanes to amides via carboxylic acid was also reported by the same research group [68]. Some amides were synthesized using methyl glycinate, di-n-propylamine, and piperidine with significant

• gave a diastereomeric mixture. A final transformation into the corresponding carboxylic acids 171 and amides 172 was performed in short reaction times (Scheme 44). Steroidal tetraoxanes showed

Methyltransferases from RiPP pathways: shaping the landscape of natural product chemistry

• Maria-Paula Schröder,
• Isabel P.-M. Pfeiffer and
• Silja Mordhorst

Beilstein J. Org. Chem. 2024, 20, 1652–1670, doi:10.3762/bjoc.20.147

• occur at the N-terminal amide, the peptide backbone, as well as on amino acid side chain amides (Figure 1). While traditional synthesis of N-methylated peptides is challenging and time consuming, installation via RiPP maturases provides an easier, quicker, and greener approach to confer these attributes

• member of the channel-forming, cytotoxic proteusins. It is biosynthesised by Microvirgula aerodenitrificans. Like polytheonamide B, aeronamide A shows cytotoxic activity against HeLa cells, with an IC50 of 1.48 nM. AerE, the PoyE homologue, installs five methylations on the amides of Asn25, Asn31, Asn37

Benzylic C(sp³)–H fluorination

• Alexander P. Atkins,
• Alice C. Dean and
• Alastair J. J. Lennox

Beilstein J. Org. Chem. 2024, 20, 1527–1547, doi:10.3762/bjoc.20.137

• yields quoted vs copper catalyst. Iron-catalysed intramolecular fluorine-atom-transfer from N–F amides. Vanadium-catalysed benzylic fluorination with Selectfluor. NDHPI-catalysed radical benzylic C(sp3)–H fluorination with Selectfluor. Potassium persulfate-mediated radical benzylic C(sp3)–H fluorination

Towards an asymmetric β-selective addition of azlactones to allenoates

• Behzad Nasiri,
• Ghaffar Pasdar,
• Paul Zebrowski,
• Katharina Röser,
• David Naderer and
• Mario Waser

Beilstein J. Org. Chem. 2024, 20, 1504–1509, doi:10.3762/bjoc.20.134

• giving access to the acyclic α-amino acid-based amides 6 straightforwardly. Experimental General details 1H and 13C NMR spectra were recorded on a Bruker Avance III 300 MHz spectrometer with a broad band observe probe. All NMR spectra were referenced on the solvent residual peak (CDCl3: δ 7.26 ppm for 1H

Hypervalent iodine-catalyzed amide and alkene coupling enabled by lithium salt activation

• Akanksha Chhikara,
• Fan Wu,
• Navdeep Kaur,
• Prabagar Baskaran,
• Alex M. Nguyen,
• Zhichang Yin,
• Anthony H. Pham and
• Wei Li

Beilstein J. Org. Chem. 2024, 20, 1405–1411, doi:10.3762/bjoc.20.122

• simple lithium salts for hypervalent iodine catalyst activation. The activated hypervalent iodine catalyst allows the intermolecular coupling of soft nucleophiles such as amides onto electronically activated olefins with high regioselectivity. Keywords: amide coupling; hypervalent iodine catalysis

• will then enable soft nucleophiles such as unadorned amides to readily participate in the ensuing olefin addition. In this regard, we wondered if the hypervalent iodine with difluoro ligands could undergo salt metathesis with lithium salts such as LiBF4 or LiPF6 to afford the more reactive cationic

• electrophilicity of the halogen source could be modulated to render different classes of nucleophiles for additions onto olefins in various olefin difunctionalization reactions [48][49][50][51][52]. In particular, we demonstrated that addition of either a Lewis acid or a base could activate amides to couple with

The Ugi4CR as effective tool to access promising anticancer isatin-based α-acetamide carboxamide oxindole hybrids

• Carolina S. Marques,
• Aday González-Bakker and
• José M. Padrón

Beilstein J. Org. Chem. 2024, 20, 1213–1220, doi:10.3762/bjoc.20.104

• structure–activity relationships derived from the GI50 values. The presence of a nitro group at the furan moiety enhanced the activity (8d > 8m). Presumably, the nitro group made 8d the most potent analogue bearing an aromatic amide (8c, 8e, 8g, 8i, 8l–n). For the aliphatic amides, the most potent

Manganese-catalyzed C–C and C–N bond formation with alcohols via borrowing hydrogen or hydrogen auto-transfer

• Mohd Farhan Ansari,
• Atul Kumar Maurya,
• Abhishek Kumar and
• Saravanakumar Elangovan

Beilstein J. Org. Chem. 2024, 20, 1111–1166, doi:10.3762/bjoc.20.98

• , which leads to the formation of a considerable amount of waste [52][53][54]. The BH approach allows a sustainable way for building C–C bonds by coupling abundant and cheap alcohols with ketones, nitriles, esters, and amides [4]. C–C Bond formation via alkylation of ketones with alcohols Several

• the same year, Milstein and co-workers accomplished the α-alkylation of esters, ketones, and amides using alcohols as alkylating agents with a PNP-pincer-supported manganese catalyst [59]. First, the α-alkylation of ketones with benzylic and aliphatic alcohols was studied using Mn11 (1 mol %) as

• catalyst and t-BuOK as a base at 125 °C for 18 h in toluene which afforded up to 95% yield of the desired alkylated ketones (Scheme 28A). Later, the more challenging esters and amides were selectively alkylated with alcohols, however, required higher catalyst loading (5 mol %) and a stoichiometric amount

Carbonylative synthesis and functionalization of indoles

• Alex De Salvo,
• Raffaella Mancuso and
• Xiao-Feng Wu

Beilstein J. Org. Chem. 2024, 20, 973–1000, doi:10.3762/bjoc.20.87

• of amides from 2-alkynylanilines by using TFBen (benzene-1,3,5-triyl triformate) as a CO source, Pd(OAc)2, DPEPhos (bis[(2-diphenylphosphino)phenyl] ether), and DIPEA (N,N-diisopropylethylamine) in MeCN. After 24 h, Pd(OAc)2 and AlCl3 were added to promote a selective cyclization reaction [14]. The

• controllable and regioselective synthesis of indol-3-α-ketoamides and indol-3-amides via the direct double- and monoaminocarbonylation of indole derivatives by using secondary amines [70]. They used Pd(dppf)Cl2 as catalyst system. The indol-3-α-ketoamides were synthesized by adding dppf as ligand, CuI as co

• -catalyst, and LiCl as additive under 40 bar of CO. To make the process regioselective towards indol-3-amides, dppf as ligand, the base (K2CO3), and I2 were added, and the reaction run under a low pressure of CO (1 bar), in addition to the catalyst. Both processes took place well in THF (Scheme 39). In 2013

Direct synthesis of acyl fluorides from carboxylic acids using benzothiazolium reagents

• Lilian M. Maas,
• Alex Haswell,
• Rory Hughes and
• Matthew N. Hopkinson

Beilstein J. Org. Chem. 2024, 20, 921–930, doi:10.3762/bjoc.20.82

• different amides, including dipeptides, under mild and operationally simple conditions in high yields. Mechanistic studies suggest that BT-SCF3 can generate acyl fluorides from carboxylic acids via two distinct pathways, which allows the deoxyfluorinating reagent to be employed in sub-stoichiometric amounts

• . Keywords: acyl fluorides; amides; benzothiazolium salts; carboxylic acids; deoxygenative reactions; Introduction Acyl fluorides are attracting much attention as versatile reagents for different applications in organic synthesis. In addition to their use as sources of fluoride ions, they are most commonly

• acyl fluoride products directly from carboxylic acids. Here, we report the results of this study, which led to the development of a practical and high yielding methodology for the synthesis of acyl fluorides and their subsequent one-pot conversion into amides. Moreover, by virtue of BT-SCF3’s ability

Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

• Jens Frackenpohl,
• David M. Barber,
• Guido Bojack,
• Birgit Bollenbach-Wahl,
• Ralf Braun,
• Rahel Getachew,
• Sabine Hohmann,
• Kwang-Yoon Ko,
• Karoline Kurowski,
• Bernd Laber,
• Rebecca L. Mattison,
• Thomas Müller,
• Anna M. Reingruber,
• Dirk Schmutzler and
• Andrea Svejda

Beilstein J. Org. Chem. 2024, 20, 540–551, doi:10.3762/bjoc.20.46

• , 15a, and 15c, the desired 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines 7a–c were prepared in good yield (Table 1, entries 15–17, 59–66% isolated yield), enabling us to investigate the biological profiles as well as the reactions with acyl chlorides to form amides 16a–f (Scheme 2) [27]. These acylations

Ligand effects, solvent cooperation, and large kinetic solvent deuterium isotope effects in gold(I)-catalyzed intramolecular alkene hydroamination

• Ruichen Lan,
• Brock Yager,
• Yoonsun Jee,
• Cynthia S. Day and
• Amanda C. Jones

Beilstein J. Org. Chem. 2024, 20, 479–496, doi:10.3762/bjoc.20.43

• have been masked by the high temperatures and long reaction times of early reports. For example, Widenhoefer engaged carbamates and amides in dioxane at temperatures >80 °C [12][13]. Later work showed that ureas could be engaged at room temperature when a NHC–gold catalyst system was used, outpacing

• nitrogen. Thus, the rate of intramolecular hydroamination is enhanced by a more nucleophilic nitrogen. Another qualitative interpretation is that rates are enhanced by carbonyl basicity. Gas-phase basicity measurements indicate that ureas are more basic than amides [47][50], and here the most Lewis base

• . Carbamates, sulfonamides, and amides display significantly reduced reactivity, if any [56][57]. Titration experiments with MeOH-d4 (further discussion below) reveal that overall reaction rates for urea 1a and carbamate 1b appear to correlated with rates of gold-mediated N–H/D exchange which may further

Mechanisms for radical reactions initiating from N-hydroxyphthalimide esters

• Carlos R. Azpilcueta-Nicolas and
• Jean-Philip Lumb

Beilstein J. Org. Chem. 2024, 20, 346–378, doi:10.3762/bjoc.20.35

• halides [93][94], bromoalkynes [95], bromoalkanes [96], and pyridyl thioesters [97] (Scheme 26A). Likewise, the Rousseaux group has recently documented the arylation of NHPI esters obtained from cyclopropanecarboxylic acids [98] and malonic acid half amides [99], while the Reisman lab has pioneered an

Copper-promoted C5-selective bromination of 8-aminoquinoline amides with alkyl bromides

• Changdong Shao,
• Chen Ma,
• Li Li,
• Jingyi Liu,
• Yanan Shen,
• Chen Chen,
• Qionglin Yang,
• Tianyi Xu,
• Zhengsong Hu,
• Yuhe Kan and
• Tingting Zhang

Beilstein J. Org. Chem. 2024, 20, 155–161, doi:10.3762/bjoc.20.14

• , China 10.3762/bjoc.20.14 Abstract An efficient and practical method for the synthesis of C5-brominated 8-aminoquinoline amides via a copper-promoted selective bromination of 8-aminoquinoline amides with alkyl bromides was developed. The reaction proceeds smoothly in dimethyl sulfoxide (DMSO) under air

• selective C5-bromination of 8-aminoquinoline amides using carbon tetrabromide and dibromomethane under photo- and electrocatalysis conditions [27][28]. In 2017, Xia and co-workers reported a novel, mild, metal-free, and regioselective bromination of amides, wherein the organic dye eosin Y acted as the

• reaction of 8-aminoquinoline amides using activated and unactivated alkyl bromides as the bromine source (Scheme 1, reaction 4). Results and Discussion At the beginning of this investigation, N-(quinolin-8-yl)benzamide (1a) and ethyl bromoacetate (2a) were selected as model substrates to screen the

Synthesis of N-acyl carbazoles, phenoxazines and acridines from cyclic diaryliodonium salts

• Nils Clamor,
• Mattis Damrath,
• Thomas J. Kuczmera,
• Daniel Duvinage and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2024, 20, 12–16, doi:10.3762/bjoc.20.2

• Bremen, Germany 10.3762/bjoc.20.2 Abstract N-Acyl carbazoles can be efficiently produced through a single-step process using amides and cyclic diaryliodonium triflates. This convenient reaction is facilitated by copper iodide in p-xylene, using the commonly found activating ligand diglyme. We have

• tested this method with a wide range of amides and iodonium triflates, proving its versatility with numerous substrates. Beyond carbazoles, we also produced a variety of other N-heterocycles, such as acridines, phenoxazines, or phenazines, showcasing the robustness of our technique. In a broader sense

• efficient method to synthesize N-acyl carbazoles from readily available iodolium salt and amides via a ring-opening/intramolecular coupling cascade (Scheme 1c) [20][21][22][23][24][25][26][27][28][29][30]. Our group recently explored principle synthetic pathways of hetero- and carbocyclic 5- and 6-membered

Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors

• Yordanka Mollova-Sapundzhieva,
• Plamen Angelov,
• Danail Georgiev and
• Pavel Yanev

Beilstein J. Org. Chem. 2023, 19, 1804–1810, doi:10.3762/bjoc.19.132

• ., 4000 Plovdiv, Bulgaria 10.3762/bjoc.19.132 Abstract β-Keto amides were used as convenient precursors to both 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides. The utility of this approach is demonstrated with the synthesis of fourteen novel and four known quinolone derivatives, including

• natural products of microbial origin such as HHQ and its C5-congener. Two compounds with high activity against S. aureus have been identified among the newly obtained quinolones, with MICs ≤ 3.12 and ≤ 6.25 µg/mL, respectively. Keywords: antibacterial; β-keto amides; enaminones; 4-quinolones; quorum

• substituents at the C-2 position. As a way of expanding the scope of this methodology, we resorted to the α-C-acylation of β-enamino amides, a reliable reaction, the utility of which we have already demonstrated in other contexts [62][63]. Results and Discussion As the starting point of our synthetic

Benzoimidazolium-derived dimeric and hydride n-dopants for organic electron-transport materials: impact of substitution on structures, electrochemistry, and reactivity

• Swagat K. Mohapatra,
• Khaled Al Kurdi,
• Samik Jhulki,
• Georgii Bogdanov,
• John Bacsa,
• Maxwell Conte,
• Tatiana V. Timofeeva,
• Seth R. Marder and
• Stephen Barlow

Beilstein J. Org. Chem. 2023, 19, 1651–1663, doi:10.3762/bjoc.19.121

• more soluble than the iodides in THF, so were reductively dimerized to 12 in THF using Na:Hg, although reduction of 1i+PF6− failed to afford 1i2. As we have noted before for other 12 species, amides (V, Scheme 1) are encountered as both byproducts of dimer synthesis and dimer decomposition products [14

N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

• Fatemeh Doraghi,
• Seyedeh Pegah Aledavoud,
• Mehdi Ghanbarlou,
• Bagher Larijani and
• Mohammad Mahdavi

Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106

• preparation of thioesters, acyl disulfides, ketones, and amides starting from N-thiohydroxy succinimide esters (NTSEs) 1’’’, which can serve as the acylthiolating and acylating source (Scheme 32) [65]. First, they synthesized a series of N-thiohydroxy succinimide esters by treating potassium thiolates with N

• selectively transfer the acyl or acylthio moieties. Arylboronic acids 74 and amines 76 were suitable for the acyl transfer and led to ketones 78 and amides 80 as the desired products. While, Grignard reagents 75 and thiols 77 acted as soft nucleophiles and resulted in thioesters 79 and acyl disulfides 81

• intermediate led to intramolecular cyclization. In 2020, electrophilic cyclization of allylic amides 134 using N-(phenylthio)succinimide 1 in the presence of camphorsulfonic acid (CSA) as a Brønsted acid and tetrabutylammonium chloride (TBAC) led to 5-[(phenylthio)methyl]oxazoline scaffolds 135 (Scheme 57) [89

α-(Aminomethyl)acrylates as acceptors in radical–polar crossover 1,4-additions of dialkylzincs: insights into enolate formation and trapping

• Angel Palillero-Cisneros,
• Paola G. Gordillo-Guerra,
• Fernando García-Alvarez,
• Olivier Jackowski,
• Franck Ferreira,
• Fabrice Chemla,
• Joel L. Terán and
• Alejandro Perez-Luna

Beilstein J. Org. Chem. 2023, 19, 1443–1451, doi:10.3762/bjoc.19.103

• allylation of lithium (trimethylsilyl)amides prepared in situ from the parent amines by a lithiation/silylation/lithiation sequence (Table 1). Using this protocol, α-(aminomethyl)acrylates 5 and 6 derived from benzhydrylamine and aniline were prepared in high yields (Table 1, entries 1 and 2). The procedure