Progress in copper-catalyzed trifluoromethylation

• Guan-bao Li,
• Chao Zhang,
• Chun Song and
• Yu-dao Ma

Beilstein J. Org. Chem. 2018, 14, 155–181, doi:10.3762/bjoc.14.11

• -catalyzed trifluoromethylation of N-aryl acrylamides using Langlois’ reagent (CF3SO2Na) as a trifluoromethyl source and water as the reaction medium (Scheme 36). A variety of CF3-containing oxindoles bearing a quaternary carbon center were formed under this conditions. Furthermore, more CF3SO2Na (3.0 equiv

• reported by the group of Baudoin and the proposed mechanism. Trifluoromethylation of benzamides reported by the group of Tan. Trifluoromethylation of heteroarenes and electron-deficient arenes reported by the group of Qing and the proposed mechanism. Trifluoromethylation of N-aryl acrylamides using

CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation and chlorination. Part 2: Use of CF₃SO₂Cl

• Hélène Chachignon,
• Hélène Guyon and
• Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2800–2818, doi:10.3762/bjoc.13.273

• -arylacrylamides para-substituted on their aryl moiety by electron-donating or electron-withdrawing groups were converted into the corresponding oxindoles with similarly good yields. However, the reaction was compatible only with acrylamides bearing methyl or phenyl as R1 and R2 groups; for example, N-acyl and N

• acrylamides were also investigated for the realisation of cascade reactions including a trifluoromethylation step. This was notably the case of unactivated alkenes: Dolbier and co-workers showed that such compounds could be involved in photoredox-catalysed trifluoromethylation reactions, followed by a 6-exo

• /cyclisation of N-arylacrylamides using BiOBr nanosheets catalysis. Photoredox-catalysed trifluoromethylation/desulfonylation/cyclisation of N-tosyl acrylamides (bpy: 2,2’-bypyridine). Photoredox-catalysed trifluoromethylation/aryl migration/desulfonylation of N-aryl-N-tosylacrylamides. Proposed mechanism for

CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF₃SO₂Na

• Hélène Guyon,
• Hélène Chachignon and
• Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2764–2799, doi:10.3762/bjoc.13.272

•  29b) [51]. A single-electron oxidative free-radical process was ascertained for the generation of CF3•. From enynes, the iodination step was realised by I2, which was formed by a multistep redox process from I2O5. The intramolecular carbotrifluoromethylations of alkenes from acrylamides and

Synthesis of 2-aminosuberic acid derivatives as components of some histone deacetylase inhibiting cyclic tetrapeptides

• Shital Kumar Chattopadhyay,
• Suman Sil and
• Jyoti Prasad Mukherjee

Beilstein J. Org. Chem. 2017, 13, 2153–2156, doi:10.3762/bjoc.13.214

• the cross product [29]. To our delight, the reaction of 11 with anilide 13c proceeded well under our developed conditions and the CM product was obtained as a single isomer (E-). Only a few successful reports on cross metathesis with Weinreb’s amide of acrylic acid, and N-alkylated acrylamides are

Highly reactive, liquid diacrylamides via synergistic combination of spatially arranged curing moieties

• Maximilian Maier,
• Magnus S. Schmidt,
• Markus Ringwald and
• Christoph P. Fik

Beilstein J. Org. Chem. 2017, 13, 372–383, doi:10.3762/bjoc.13.40

• (meth)acrylate-based compositions, however, is their susceptibility to premature hydrolysis when used in aqueous solutions, especially at pH values <2.5 [15][16]. One strategy to improve the hydrolytic stability is the oxygen-to-nitrogen substitution. The obtained class of (meth)acrylamides is of

• interest in the field of biomedical applications, e.g., for dental materials, artificial cornea, or drug-delivery systems, for which contact with body fluids is inevitable [17][18]. Whilst some of the resulting secondary di(meth)acrylamides end up being solids, tertiary di(meth)acrylamides can be obtained

• as relatively low viscous, highly soluble/compatible liquids [19]. Furthermore, acrylamides are generally more reactive than the respective methacrylamides. Regarding the substitution pattern, N-monosubstituted acrylamides tend to homopolymerize more readily than their N,N-disubstituted analogues [20

Conjugate addition–enantioselective protonation reactions

• James P. Phelan and
• Jonathan A. Ellman

Beilstein J. Org. Chem. 2016, 12, 1203–1228, doi:10.3762/bjoc.12.116

• described the synthesis of β-aminocarbonyl compounds via the enantioselective addition of amine salts 74 to N-benzyloxycarbonyl acrylamides 75 and 77 catalyzed by a palladium-μ-hydroxo complex 79 (Scheme 18) [38][39][40]. Hii has used the same catalyst system and reported comparable yields and slightly

• cyclic N-benzyloxycarbonyl acrylamides 75 and 77 in moderate to good yields and high enantioselectivity (Scheme 18a,b). Due to their attenuated nucleophilicity, electron-deficient amines were unreactive under the standard reaction conditions. Addition of 0.5 equivalents of free amine was found to be

• . Using a cationic rhodium(I)/QuinoxP* 154 complex, Tanaka and co-workers achieved the enantioselective hydroacylation of α-substituted acrylamides 153 using aliphatic aldehydes 32 to provide 1,4-ketoamides 155 in high yields and excellent enantioselectivity (Scheme 36) [64]. A variety of aliphatic

Cationic Pd(II)-catalyzed C–H activation/cross-coupling reactions at room temperature: synthetic and mechanistic studies

• Takashi Nishikata,
• Alexander R. Abela,
• Shenlin Huang and
• Bruce H. Lipshutz

Beilstein J. Org. Chem. 2016, 12, 1040–1064, doi:10.3762/bjoc.12.99

• expanded the substrate scope to include reactions with 3-alkyl-substituted ureas, as well as a wider variety of acrylates and even some acrylamides (Figure 4, 5d–h, conditions B). Many combinations of acrylates and more challenging arylureas, however, did not produce the desired product in satisfactory

• ), while acrylamides having simple amine or amino acid moieties also participated in cross-coupling reactions with the arylurea to produce the corresponding amide derivatives in moderate to good yields (5s, 5t). Total synthesis of boscalid® via C–H activation The rationale behind the attention recently

Application of 7-azaisatins in enantioselective Morita–Baylis–Hillman reaction

• Qing He,
• Gu Zhan,
• Wei Du and
• Ying-Chun Chen

Beilstein J. Org. Chem. 2016, 12, 309–313, doi:10.3762/bjoc.12.33

• acrolein catalyzed by β-isocupreidine (β-ICD) was reported by the Zhou group [5], isatin derivatives, as highly activated electrophiles, have been utilized by other groups for similar transformations with acrylates or acrylamides, affording the 3-hydroxyoxindole derivatives with moderate to excellent

Cross metathesis of unsaturated epoxides for the synthesis of polyfunctional building blocks

• Meriem K. Abderrezak,
• Kristýna Šichová,
• Nancy Dominguez-Boblett,
• Antoine Dupé,
• Zahia Kabouche,
• Christian Bruneau and
• Cédric Fischmeister

Beilstein J. Org. Chem. 2015, 11, 1876–1880, doi:10.3762/bjoc.11.201

• generally challenging transformations as they are substrate-dependent and therefore require optimization of experimental parameters. For instance, while cross metathesis with methyl acrylate turns out to be a rather straightforward transformation, cross metatheses with acrylonitrile, acrylamides or acrolein

Chiral phosphines in nucleophilic organocatalysis

• Yumei Xiao,
• Zhanhu Sun,
• Hongchao Guo and
• Ohyun Kwon

Beilstein J. Org. Chem. 2014, 10, 2089–2121, doi:10.3762/bjoc.10.218

•  23). Shortly after, the Lu group further expanded the substrate scope of asymmetric [3 + 2] annulations with allenoates to a series of 3,5-dimethyl-1H-pyrazole-derived acrylamides (Scheme 24) [55]. The dipeptide-based phosphine H10 effectively promoted the reaction in good to excellent yields, albeit

The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids

• Tatyana L. Pavlovskaya,
• Fedor G. Yaremenko,
• Victoria V. Lipson,
• Svetlana V. Shishkina,
• Oleg V. Shishkin,
• Vladimir I. Musatov and
• Alexander S. Karpenko

Beilstein J. Org. Chem. 2014, 10, 117–126, doi:10.3762/bjoc.10.8

• , A.V. Bogatsky physico-chemical institute of the National Academy of Sciences of Ukraine, 86, Lustdorfskaya doroga, 65080, Odessa, Ukraine 10.3762/bjoc.10.8 Abstract The regioselective three-component condensation of azomethine ylides derived from isatins and α-amino acids with acrylamides or

• indolones. Keywords: acrylamides; aroylacrylic acids; azomethine ylide; cyclative rearrangement; cycloaddition; multicomponent; spirooxindoles; Introduction The design of new spirocyclic compounds is intriguing due to their unique non-planar structure and great potential for binding to biomolecules due to

• inhibitors there are compounds containing a pyrrolidine-2-one as a part of the spirocyclic system [34]. In the present work we report the synthesis of spirooxindolo pyrrolidines and pyrrolizidines by utilizing a 1,3-dipolar cycloaddition of hitherto uninvestigated acrylamides and aroylacrylic acids with

RAFT polymers for protein recognition

• Alan F. Tominey,
• Julia Liese,
• Sun Wei,
• Klaus Kowski,
• Thomas Schrader and
• Arno Kraft

Beilstein J. Org. Chem. 2010, 6, No. 66, doi:10.3762/bjoc.6.66

• , there have been no reports of the successful use of ATRP with acrylamides. In contrast, RAFT can be used in a variety of solvents and, most importantly, it is compatible with NIPAM [11][12]. For this reason, RAFT was chosen in this paper as the preferred method for controlled synthesis of linear

Pd-catalyzed decarboxylative Heck vinylation of 2-nitrobenzoates in the presence of CuF₂

• Lukas J. Gooßen,
• Bettina Zimmermann and
• Thomas Knauber

Beilstein J. Org. Chem. 2010, 6, No. 43, doi:10.3762/bjoc.6.43

• regard to the olefin substrate. As shown in Table 2, styrenes, acrylate esters, and even acrylamides were coupled in good yields. In all cases, the reaction proceeded with high selectivities for the (E)-configured linear products. Other isomers were detected in trace amounts only. Next, we examined the

N-alkyl-N-(phosphonoethyl) substituted (meth)acrylamides – new adhesive monomers for self-etching self-priming one part dental adhesive

• Joachim E. Klee and
• Uwe Lehmann

Beilstein J. Org. Chem. 2009, 5, No. 72, doi:10.3762/bjoc.5.72

• Joachim E. Klee Uwe Lehmann Dentsply De Trey, De-Trey-Str. 1, 78467 Konstanz, Germany 10.3762/bjoc.5.72 Abstract Novel N-alkyl-N-(phosphonoethyl) substituted mono-, bis- and tris(meth)acrylamides 3 were synthesized by two different three-step reactions and characterized by IR, 1H NMR and 13C NMR

• spectroscopy as well as refractive index and viscosity. The phosphonoethyl substituted (meth)acrylamide monomers show improved hydrolytic stability compared to carboxylic esters. The highest stability was found for the phosphonoethyl substituted acrylamide monomers. Acrylamides have a larger polymerization

• enthalpy ranging from −50 to −70 kJ·mol−1 per double bond compared to methacrylamides which show −8.57 to −25.1 kJ·mol−1 per double bond. Depending on their structure (meth)acrylamides 3 exhibit an adhesion to enamel and dentin up to 19.5 MPa. The monomer 3c shows the highest adhesion values to both