Formal γ-C(sp3)-H Activation of Ketones via Microwave-Promoted and Iminyl-Radical-Mediated 1,5-Hydrogen Atom Transfer

被引：6

作者：

Singh, Jatinder ^{[1
]}

Jones, Spencer A. ^{[1
]}

Nelson, Tanner J. ^{[1
]}

Botello, Jesus A. ^{[1
]}

Castle, Steven L. ^{[1
]}

机构：

[1] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 14期

基金：

美国国家科学基金会;

关键词：

GAMMA-ALKYLATION; CARBONYL; ETHERS; FUNCTIONALIZATIONS; ARYLATION; OXIMES; BOND;

D O I：

10.1021/acs.joc.3c00915

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Microwave irradiation of O-phenyloximes triggersN-O homolysis and 1,5-hydrogen atom transfer (HAT), resultingin formal & gamma;-C-H functionalization of ketones after trappingof the radical intermediate and in situ imine hydrolysis.The Lewis acid InCl3 & BULL;H2O facilitated HAT,enabling functionalization of benzylic and nonbenzylic secondary carbonatoms. Functionalization of primary carbons was feasible but affordedlow yields, requiring ClCH2CO2H instead of InCl3 & BULL;H2O as an additive. C-O and C-Cbond formation could both be accomplished by this method.

引用

收藏

页码：10287 / 10297

页数：11

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