Deoxygenative Insertion of Carbonyl Carbon into a C(sp3)-H Bond: Synthesis of Indolines and Indoles

被引：42

作者：

Asako, Sobi ^{[1
,2
]}

Ishihara, Seina ^{[1
]}

Hirata, Keiya ^{[1
]}

Takai, Kazuhiko ^{[1
]}

机构：

[1] Okayama Univ, Div Appl Chem, Grad Sch Nat Sci & Technol, Kita Ku, 3-1-1 Tsushimanaka, Okayama 7008530, Japan

[2] RIKEN Ctr Sustainable Resource Sci, 2-1 Hirosawa, Wako, Saitama 3510198, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2019年 / 141卷 / 25期

关键词：

C-H ACTIVATION; OXIDATIVE ADDITION; STRUCTURAL-CHARACTERIZATION; DITUNGSTEN HEXAALKOXIDES; DIRECT FUNCTIONALIZATION; ORGANIC-SYNTHESIS; TERTIARY-AMINES; OXO-ALKYLIDENE; KETONES; CHEMISTRY;

D O I：

10.1021/jacs.9b05428

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple deoxygenation reagent prepared in situ from commercially available Mo(CO)(6) and orthoquinone has been developed for the synthesis of indoline and indole derivatives. The Mo/quinone complex efficiently deoxygenates carbonyl compounds bearing a neighboring dialkylamino group and effects intramolecular cyclizations with the insertion of a deoxygenated carbonyl carbon into a C(sp(3))-H bond, in which a carbonyl group acts as a carbene equivalent. The reaction also proceeds with a catalytic amount of Mo/quinone in the presence of disilane as an oxygen atom acceptor.

引用

页码：9832 / 9836

页数：5

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