分子内 sp2 C-H 和 sp3 C-H 键的脱氢偶联：合成 2-氧吲哚的快捷途径。

Intramolecular dehydrogenative coupling of sp2 C-H and sp3 C-H bonds: an expeditious route to 2-oxindoles.

机构信息

Department of Chemistry, Indian Institute of Science Education and Research Bhopal, MP-462 023, India.

出版信息

Org Lett. 2012 Dec 7;14(23):5864-7. doi: 10.1021/ol302767w. Epub 2012 Nov 7.

Abstract

An intramolecular-dehydrogenative-coupling (IDC) using "transition-metal-free" oxidation conditions has been achieved to synthesize a variety of 2-oxindoles bearing an all-carbon quaternary stereogenic center at the benzylic position. The methodology involves a one-pot C-alkylation of β-N-arylamido esters (3, 6) with alkyl halides using potassium tert-butoxide concomitant with a dehydrogenative coupling. A radical-mediated pathway has been tentatively proposed for the oxidative process.

摘要

已实现一种分子内脱氢偶联（IDC），使用“无过渡金属”氧化条件合成各种带有苄位全碳季立体中心的 2-氧吲哚。该方法包括使用叔丁醇钾一锅法用烷基卤化物对β-N-芳酰胺酯（3、6）进行 C-烷基化，同时进行脱氢偶联。对于氧化过程，已初步提出自由基介导途径。