Hydroarylations by cobalt-catalyzed C–H activation

• Rajagopal Santhoshkumar and
• Chien-Hong Cheng

Beilstein J. Org. Chem. 2018, 14, 2266–2288, doi:10.3762/bjoc.14.202

• . Protonation and isomerization generate cobalt complex G4, which is converted into alkenated product 54 by ligand exchange. 4. Hydroarylation of enynes Catalytic cyclization of 1,n-enynes has become as an attractive tool for the preparation of cyclic adducts with a variety of functionalities in a one-pot

• process [92]. As the cyclization of 1,n-enynes with organometallics is well-known, the addition of an inert C–H bond to 1,n-enynes further enhances the economy of cyclization process. Thus, Cheng and co-workers reported a cobalt-catalyzed hydroarylative cyclization of 1,n-enynes with carbonyl compounds 55

Glycosylation reactions mediated by hypervalent iodine: application to the synthesis of nucleosides and carbohydrates

• Yuichi Yoshimura,
• Hideaki Wakamatsu,
• Yoshihiro Natori,
• Yukako Saito and
• Noriaki Minakawa

Beilstein J. Org. Chem. 2018, 14, 1595–1618, doi:10.3762/bjoc.14.137

• yields for the one-pot process are comparable or superior to those obtained with the two-step procedure (Scheme 18). Synthesis of disaccharides Classically, carbohydrates have been considered primarily an energy source for life – as in the cases of glucose, fructose and their oligosaccharides, e.g

Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination

• Jiyun Sun,
• Xiaohua Zhen,
• Huaibin Ge,
• Guangtao Zhang,
• Xuechan An and
• Yunfei Du

Beilstein J. Org. Chem. 2018, 14, 1452–1458, doi:10.3762/bjoc.14.123

• (PhIO)-mediated intramolecular azirination in a one-pot process. Keywords: azirination; 2H-azirine; iodosobenzene; Togni reagent; β-trifluoromethylation; Introduction The trifluoromethyl group is a striking structural motif, which can be widely found in the fields of pharmaceutical and agrochemical

• skeleton bearing versatile substituents, we herein report that the biologically interesting CF3 group can be incorporated into the privileged 2H-azirine framework through the Togni reagent 1-mediated trifluoromethylation followed by PhIO-mediated azirination in a one-pot process. Results and Discussion It

• -trifluoromethylated 2H-azirine 7a in a yield of 60% (Scheme 2). In order to make the synthesis of β-trifluoromethylated 2H-azirine more concise and convenient, we were keen to probe whether the two-step synthesis could be combined into a one-pot process. For this purpose, we first carried out the reaction of Togni

An efficient and facile access to highly functionalized pyrrole derivatives

• Meng Gao,
• Wenting Zhao,
• Hongyi Zhao,
• Ziyun Lin,
• Dongfeng Zhang and
• Haihong Huang

Beilstein J. Org. Chem. 2018, 14, 884–890, doi:10.3762/bjoc.14.75

• oxidation protocol. With the optimized reaction conditions for each step in hand, we prepared 12a starting from benzaldehyde and ethyl glycinate hydrochloride through three steps but via a one-pot process without any purification for intermediates 9a and 11a (see Supporting Information File 1). To our

• benzaldehydes bearing electron-withdrawing or electron-donating substituents on the phenyl ring reacted smoothly via condensation–cycloaddition–oxidation in the one-pot process, delivering the corresponding pyrrolo[3,4-c]pyrrole-1,3-diones in moderate to good yields (53–77%). Heteroaromatic aldehydes 7i and 7j

Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols

• Xinyun Liu,
• Johnny H. Phan,
• Benjamin J. Haugeberg,
• Shrikant S. Londhe and
• Michael D. Clift

Beilstein J. Org. Chem. 2017, 13, 2895–2901, doi:10.3762/bjoc.13.282

• this reaction sequence, (thio)silyl ketene acetal 10 was united with 2-phenylglycinol and para-anisidine in a two-step, one-pot process to provide β-amino acid derivative 11 in a 60% yield. The overall reaction sequence provides a unique method for the production of the high-value β-amino acid

One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P^® activation of 3-arylpropiolic acids

• Melanie Denißen,
• Alexander Kraus,
• Guido J. Reiss and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2017, 13, 2340–2351, doi:10.3762/bjoc.13.231

• one-pot process. Here, we report the development of the one-pot synthesis of these title compounds by a consecutive pseudo three-component approach and the investigation of the luminescence behavior by absorption and emission spectroscopy. Results and Discussion Synthesis and structure of 4

Preparation of imidazo[1,2-a]-N-heterocyclic derivatives with gem-difluorinated side chains

• Layal Hariss,
• Kamal Bou Hadir,
• Mirvat El-Masri,
• Thierry Roisnel,
• René Grée and
• Ali Hachem

Beilstein J. Org. Chem. 2017, 13, 2115–2121, doi:10.3762/bjoc.13.208

• DBU (1,8-diazabicycloundec-7-ene) under the same conditions as mentioned above, the desired imidazopyridine derivative 7a was isolated in 33% yield (Scheme 4). This one-pot process gives an overall yield very close to the two-step reaction (38%). Further, the halogen-substituted substrate 7e appeared

Synthesis of benzothiophene and indole derivatives through metal-free propargyl–allene rearrangement and allyl migration

• Jinzhong Yao,
• Yajie Xie,
• Lianpeng Zhang,
• Yujin Li and
• Hongwei Zhou

Beilstein J. Org. Chem. 2017, 13, 1866–1870, doi:10.3762/bjoc.13.181

• -pot process. Based on our understanding of organosulfur chemistry [20][21][22], we report herein a simple, metal-free method for the formation of benzothiophenes using an intramolecular addition of a sulfur atom (originated from a sulfide) to the electron-deficient allene moiety generated in situ by a

• heterocycles are not well-documented [30][31]. Recently, our group explored the utilization of β-sulfonium carbanions for the preparation of thiophene derivatives [19]. Alkynes were treated with acyl chloride under Sonogashira reaction conditions and the expected β-sulfonium carbanions were obtained in a one

Total syntheses of the archazolids: an emerging class of novel anticancer drugs

• Stephan Scheeff and
• Dirk Menche

Beilstein J. Org. Chem. 2017, 13, 1085–1098, doi:10.3762/bjoc.13.108

• efforts had to be invested, before acid 21 could be efficiently obtained as shown in Scheme 4. Finally, after optimization of a reported procedure [73] the successful route employed a one-pot process involving a sodium hydride-mediated coupling of methyl malonate 19 with iodoform (20) followed by a

A practical and efficient approach to imidazo[1,2-a]pyridine-fused isoquinolines through the post-GBB transformation strategy

• Taofeng Shao,
• Zhiming Gong,
• Tianyi Su,
• Wei Hao and
• Chao Che

Beilstein J. Org. Chem. 2017, 13, 817–824, doi:10.3762/bjoc.13.82

• clinical trials [14]. Multicomponent reactions (MCRs) [15][16][17][18][19], comprising three or more components, provide straightforward approaches to a wide range of heterocycles through the formation of various bonds in a one-pot process. These reactions not only greatly accelerate chemical syntheses [20

Synthesis of 1-indanones with a broad range of biological activity

• Marika Turek,
• Dorota Szczęsna,
• Marek Koprowski and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48

• 11 (X = H/OH) and 2-(trifluoromethyl)acrylic acid (10) as a result of a Friedel–Crafts alkylation. An efficient and scalable one-pot process for the preparation of 1-indanones from benzoic acids has been described by Huang et al. [18]. In this synthesis, acyl chlorides formed in the reaction of

• ketoesters 59. The base-mediated cyclization of the latter in the presence of sodium ethoxide led to the formation of the corresponding 1-indanone anions α to carbonyl, which next were alkylated to give 2-substituted 1-indanones 60 (Scheme 20). This one-pot process utilizing a multi-task palladium catalyst

Benzothiadiazole oligoene fatty acids: fluorescent dyes with large Stokes shifts

• Lukas J. Patalag and
• Daniel B. Werz

Beilstein J. Org. Chem. 2016, 12, 2739–2747, doi:10.3762/bjoc.12.270

• same length, but of more extended conjugation we made use of the Horner–Wadsworth–Emmons (HWE) reaction. Phosphonate 4 was reacted with the respective aldehyde 1. In a facile three-step one-pot process the emerging α,β-unsaturated ester 5 was immediately converted to the alcohol 6 in 87% yield in the

Et₃B-mediated and palladium-catalyzed direct allylation of β-dicarbonyl compounds with Morita–Baylis–Hillman alcohols

• Ahlem Abidi,
• Yosra Oueslati and
• Farhat Rezgui

Beilstein J. Org. Chem. 2016, 12, 2402–2409, doi:10.3762/bjoc.12.234

• interesting synthesis of bicyclic dienones in a one-pot process involving the reaction of 2-(acetoxymethyl)cyclohex-2-enone with 1,3-dicarbonyl compounds using K2CO3 as a weak base. Later, Chamakh and Amri [38] have described a one-pot synthesis of (E)-4-alkylidene-2-cyclohexen-1-ones through a cross coupling

Rearrangements of organic peroxides and related processes

• Ivan A. Yaremenko,
• Vera A. Vil’,
• Dmitry V. Demchuk and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162

Aluminacyclopentanes in the synthesis of 3-substituted phospholanes and α,ω-bisphospholanes

• Vladimir A. D’yakonov,
• Alevtina L. Makhamatkhanova,
• Rina A. Agliullina,
• Leisan K. Dilmukhametova,
• Tat’yana V. Tyumkina and
• Usein M. Dzhemilev

Beilstein J. Org. Chem. 2016, 12, 406–412, doi:10.3762/bjoc.12.43

• efficient one-pot process for the synthesis of 3-substituted phospholanes and α,ω-bisphospholanes was developed. The method involves the replacement of aluminium in aluminacyclopentanes, prepared in situ by catalytic cycloalumination of α-olefins and α,ω-diolefins, by phosphorus atoms on treatment with

Recent developments in copper-catalyzed radical alkylations of electron-rich π-systems

• Kirk W. Shimkin and
• Donald A. Watson

Beilstein J. Org. Chem. 2015, 11, 2278–2288, doi:10.3762/bjoc.11.248

• dihydrofurans could be easily converted into furans using DDQ in a one-pot process. In addition to α-bromo esters and ketones, Lei and co-workers have also recently shown that benzylic halides could undergo radical alkenylation via copper catalysis [39]. By exploiting the propensity of benzyl halides to form

Cross-metathesis of polynorbornene with polyoctenamer: a kinetic study

• Yulia I. Denisova,
• Maria L. Gringolts,
• Alexander S. Peregudov,
• Liya B. Krentsel,
• Ekaterina A. Litmanovich,
• Arkadiy D. Litmanovich,
• Eugene Sh. Finkelshtein and
• Yaroslav V. Kudryavtsev

Beilstein J. Org. Chem. 2015, 11, 1796–1808, doi:10.3762/bjoc.11.195

• obtaining unsaturated statistical copolymers, especially promising for the comonomers with considerably different polymerization rates, it would be interesting to also try a one-pot process, in which case the reaction starts with a monomeric mixture of COE and NB. This could eliminate tedious procedures of

Radical-mediated dehydrative preparation of cyclic imides using (NH₄)₂S₂O₈–DMSO: application to the synthesis of vernakalant

• Dnyaneshwar N. Garad,
• Subhash D. Tanpure and
• Santosh B. Mhaske

Beilstein J. Org. Chem. 2015, 11, 1008–1016, doi:10.3762/bjoc.11.113

• convenient one-pot process for the synthesis of miscellaneous cyclic imides in high yields starting from readily available primary amines and cyclic anhydrides. A plausible radical mechanism involving DMSO has been proposed. The application of this facile one-pot imide forming process has been demonstrated

• a convenient one-pot process for the preparation of structurally diverse cyclic imides starting from readily available primary amines and cyclic anhydrides using APS–DMSO as an efficient and novel dehydrating reagent and its application to a drug synthesis. The scope of the developed protocol was

Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes

• Yibiao Li,
• Liang Cheng,
• Xiaohang Liu,
• Bin Li and
• Ning Sun

Beilstein J. Org. Chem. 2014, 10, 2886–2891, doi:10.3762/bjoc.10.305

• annulation reactions are iodides and bromides. It is rare to employ aryl fluorides because of their low reactivity [31][32][33]. To extend the application of our strategy of the copper-catalyzed synthesis of heterocycles, we report herein a one-pot process for the synthesis of benzo[b]furans and benzo[b

Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

• Thilo Focken and
• Stephen Hanessian

Beilstein J. Org. Chem. 2014, 10, 1848–1877, doi:10.3762/bjoc.10.195

Primary-tertiary diamine-catalyzed Michael addition of ketones to isatylidenemalononitrile derivatives

• Akshay Kumar and
• Swapandeep Singh Chimni

Beilstein J. Org. Chem. 2014, 10, 929–935, doi:10.3762/bjoc.10.91

• one pot providing Michael product 4a in a good yield of 80% and a high enantioselectivity of 98% ee (Scheme 3). The slightly lower yield of the one-pot process compared to the stepwise process was due to the competing reaction of isatin and acetone to form aldol adduct 5 (8% yield). The reaction

Boron-substituted 1,3-dienes and heterodienes as key elements in multicomponent processes

• Ludovic Eberlin,
• Fabien Tripoteau,
• François Carreaux,
• Andrew Whiting and
• Bertrand Carboni

Beilstein J. Org. Chem. 2014, 10, 237–250, doi:10.3762/bjoc.10.19

• three-component process (Scheme 3) [34]. Extension of this work to the intramolecular version is depicted in Scheme 4. The bicyclic lactone 1 was obtained stereoselectively from a diene-yne in a one-pot process with control of the relative stereochemistry of the five stereogenic centers [35]. Concerning

• diastereomers (Scheme 25). No formation of products resulting from a first cycloaddition of the 1,3-butadienyl moiety was observed when these reactions were conducted in a tandem one-pot process. Various transformations were further carried out as oxidation with hydrogen peroxide or addition to aldehydes that

One-pot cross-enyne metathesis (CEYM)–Diels–Alder reaction of gem-difluoropropargylic alkynes

• Santos Fustero,
• Paula Bello,
• Javier Miró,
• María Sánchez-Roselló,
• Günter Haufe and
• Carlos del Pozo

Beilstein J. Org. Chem. 2013, 9, 2688–2695, doi:10.3762/bjoc.9.305

• fluorinated amides 1 [23][24][25] and compounds 3b,c,e,g,h,j,l,n [29] were previously described. General procedure for the one-pot process. Ethylene was bubbled through a solution of catalyst I (5 mol %) in dry toluene (2.4 mL) for 3 minutes at room temperature in a sealed tube. Substrate 1 (0.12–0.25 mmol

AgOTf-catalyzed one-pot reactions of 2-alkynylbenzaldoximes with α,β-unsaturated carbonyl compounds

• Qiuping Ding,
• Dan Wang,
• Puying Luo,
• Meiling Liu,
• Shouzhi Pu and
• Liyun Zhou

Beilstein J. Org. Chem. 2013, 9, 1949–1956, doi:10.3762/bjoc.9.231

• assumed route, we started to investigate the possibility of this one-pot process. Results and Discussion Initially, a set of experiments was carried out with 2-alkynylbenzaldoxime 1a and methyl methacrylate (2a) as model substrates in the presence of AgOTf (5 mol %). As expected, the reaction proceeded

• that this one-pot process was highly efficient to construct 1-alkylated isoquinolines under very mild conditions. With the optimized conditions in hand, the scope of the procedure was investigated for the reaction of 2-(p-tolylethynyl)benzaldehyde oxime (1b) with a series of α,β-unsaturated carbonyl

Synthesis of enones, pyrazolines and pyrrolines with gem-difluoroalkyl side chains

• Assaad Nasr El Dine,
• Ali Khalaf,
• Danielle Grée,
• Olivier Tasseau,
• Fares Fares,
• Nada Jaber,
• Philippe Lesot,
• Ali Hachem and
• René Grée

Beilstein J. Org. Chem. 2013, 9, 1943–1948, doi:10.3762/bjoc.9.230

• -mediated isomerisation affords enones in fair yields with a gem-difluoroalkyl chain. These derivatives were used to prepare pyrazolines and pyrrolines with the desired gem-difluoroalkyl side chain by cyclocondensations in good yields and with excellent stereoselectivity. A one-pot process was also