Efficacy of radical reactions of isocyanides with heteroatom radicals in organic synthesis

• Akiya Ogawa and
• Yuki Yamamoto

Beilstein J. Org. Chem. 2024, 20, 2114–2128, doi:10.3762/bjoc.20.182

• phenanthridines via silver-catalyzed radical sulfonylation–cyclization of 2-isocyanobiphenyls (Scheme 25) [98]. Wang et al. reported a radical borylative cyclization of 2-isocyanobiaryls with N-heterocyclic carbene borane (Scheme 26) [99]. The boryl radical generated via hydrogen abstraction in the presence of di

Visible light-mediated difluoroalkylation of electron-deficient alkenes

• Vyacheslav I. Supranovich,
• Vitalij V. Levin,
• Marina I. Struchkova,
• Jinbo Hu and
• Alexander D. Dilman

Beilstein J. Org. Chem. 2018, 14, 1637–1641, doi:10.3762/bjoc.14.139

• energetic UV light (xenon arc lamp) in combination with sodium cyanoborohydride to trigger the reaction of non-fluorinated alkyl iodides [45][46][47]. Subsequently, we showed that silyldifluoromethyl iodide can generate the corresponding gem-difluorinated radical in combination with an N-heterocyclic

• carbene/borane complex and 400 nm light [48]. Results and Discussion Iodide 1a was selected as a model substrate and its reaction with tert-butyl acrylate (2a) was evaluated in the presence of various boron hydrides (Table 1). The reaction was performed in methanol with irradiation by a strip of blue

Reductions of aldehydes and ketones with a readily available N-heterocyclic carbene borane and acetic acid

• Vladimir Lamm,
• Xiangcheng Pan,
• Tsuyoshi Taniguchi and
• Dennis P. Curran

Beilstein J. Org. Chem. 2013, 9, 675–680, doi:10.3762/bjoc.9.76

• Vladimir Lamm Xiangcheng Pan Tsuyoshi Taniguchi Dennis P. Curran Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260 USA 10.3762/bjoc.9.76 Abstract Acetic acid promotes the reduction of aldehydes and ketones by the readily available N-heterocyclic carbene borane, 1,3

• scale, products are isolated by evaporation of the reaction mixture and direct chromatography. Keywords: NHC-borane; N-heterocyclic carbene borane; reduction; Introduction Reduction of carbonyl compounds is a common, fundamental chemical transformation. Among the numerous hydride reagents available