期刊
ACS CATALYSIS
卷 8, 期 9, 页码 8430-8440出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b02361
关键词
redox catalysis; Lewis acid; C-H activation; dehydrogenative; dual iron activation; hydrocarbon; alpha-alkylation; quaternary carbon center
资金
- JSPS KAKENHI [JP15H05846, JP16H01032, 16K08166]
- AMED [JP17am0101091]
- Sumitomo Foundation
Chemoselective iron-catalyzed dehydrogenative cross-coupling using 2-acylimidazoles is described. The addition of a phosphine oxide ligand substantially facilitated the generation of tert-butoxy radicals from di-tert-butyl peroxide, allowing for efficient benzylic C-H bond cleavage under mild conditions. Extensive mechanistic studies revealed that the enolization of 2-acylimidazole proceeded through dual iron catalyst activation, followed by subsequent chemo-selective cross-coupling with a benzyl radical over an undesired benzyl radical-derived homocoupling dimer that inevitably formed in earlier reported conditions. A variety of alkylarenes, aliphatic alkane, and functionalized 2-acylimidazoles were applicable, demonstrating the synthetic utility of the present catalysis. Contiguous all-carbon quaternary carbons were constructed through dehydrogenative cross-coupling. The catalytic chemoselective activation of 2-acylimidazole over bidentate coordinative and much more acidic malonate diester was particular noteworthy. Catalytic oxidative cross-enolate coupling of two distinct carboxylic acid equivalents was also achieved using acetonitrile as a coupling partner.
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