Interception of Cobalt-Based Carbene Radicals with α-Aminoalkyl Radicals: A Tandem Reaction for the Construction of β-Ester-γ-amino Ketones

被引：75

作者：

Zhang, Jie ^{[1
]}

Jiang, Jiewen ^{[1
]}

Xu, Dongmei ^{[1
]}

Luo, Qiang ^{[1
]}

Wang, Hongxiang ^{[1
]}

Chen, Jijun ^{[1
]}

Li, Huihuang ^{[1
]}

Wang, Yaxiong ^{[1
]}

Wan, Xiaobing ^{[1
]}

机构：

[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 04期

关键词：

carbene radicals; cobalt; Kornblum-DeLaMare reaction; radical reactions; tandem reactions; ASYMMETRIC INTRAMOLECULAR CYCLOPROPANATION; THEORETICAL-ANALYSIS; DIAZO-COMPOUNDS; COMPLEXES; ALKENES; FUNCTIONALIZATION; DECOMPOSITION; CYCLIZATION; MECHANISM; OXINDOLES;

D O I：

10.1002/anie.201408874

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The interception of cobalt-based carbene radicals with -aminoalkyl radicals was combined with the Kornblum-DeLaMare reaction and provides -ester--amino ketones, which are otherwise difficult to obtain in high chemoselectivity. Mechanistically, this transformation is an interplay of cobalt-based carbene radicals, organoradicals, and ionic intermediates and involves the construction of two CC bonds and one CO bond in a one-pot process. The reaction also features a wide substrate scope and is highly efficient and insensitive to moisture and air.

引用

页码：1231 / 1235

页数：5

共 62 条

[11] Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion [J].