通过 C-C/N-O 键断裂和 C-H 官能化实现环丁酮肟酯参与的[2+2+1]碳环化反应，构建 1,7-烯炔的一碳单元。

One-Carbon Incorporation Using Cyclobutanone Oxime Ester Enabled [2 + 2 + 1] Carboannulation of 1,7-Enynes by C-C/N-O Bond Cleavage and C-H Functionalization.

机构信息

State Key Laboratory of Chemo/Biosensing and Chemometrics , Hunan University , Changsha 410082 , China.

Key Laboratory of Functional Metal-Organic Compounds of Hunan Province, Key Laboratory of Functional Organometallic Materials, University of Hunan Province , Hengyang Normal University , Hengyang 421008 , China.

出版信息

Org Lett. 2019 Dec 6;21(23):9434-9437. doi: 10.1021/acs.orglett.9b03643. Epub 2019 Nov 25.

DOI:10.1021/acs.orglett.9b03643

PMID:31762279

Abstract

A NiCl-promoted [2 + 2 + 1] carboannulation of 1,7-enynes with internally oxidative cyclobutanone oximes to produce canyo-functionalized 4-cyclopenta[]quinolin-4-ones is disclosed. Through C-C/N-O bond cleavage and C-H functionalization, the process enables one-carbon incorporation using cyclobutanone oximes to achieve [2 + 2 + 1] carboannulation of 1,7-enynes, which is highlighted by allowing the formation of four new bonds with high selectivity and broad substrate scope.

摘要

一种 NiCl 促进的 1,7-烯炔与内氧化环丁酮肟的 [2 + 2 + 1] 碳环化反应，生成可烷氧基化的 4-环戊并[]喹啉-4-酮，被披露出来。通过 C-C/N-O 键的断裂和 C-H 官能化，该过程使用环丁酮肟实现了一碳的掺入，从而实现了 1,7-烯炔的 [2 + 2 + 1] 碳环化，该过程的特点是具有高选择性和广泛的底物范围，能够形成四个新的键。