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钯催化二芳基胺与α,β-不饱和酸的[3+3]环化反应:通过 C-H 活化直接构建 4-取代的 2-喹啉酮。

Palladium-Catalyzed [3+3] Annulation between Diarylamines and α,β-Unsaturated Acids through C-H Activation: Direct Access to 4-Substituted 2-Quinolinones.

机构信息

Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076 (India).

出版信息

Chemistry. 2015 Jun 1;21(23):8360-4. doi: 10.1002/chem.201500774. Epub 2015 Apr 21.

DOI:10.1002/chem.201500774
PMID:25899388
Abstract

A C-H activation strategy has been successfully employed for the high-yielding synthesis of a diverse array of 4-substituted 2-quinolinone species by a palladium-catalyzed dehydrogenative coupling involving diarylamines. This intermolecular annulation approach incorporates readily available α,β-unsaturated carboxylic acids as the coupling partner by suppressing the facile decarboxylation. Based on preliminary mechanistic studies, a reaction sequence is proposed, involving ortho palladation, π-coordination, β-migratory insertion, and β-hydride elimination.

摘要

一种 C-H 活化策略已成功应用于通过钯催化的涉及二苯胺的脱氢偶联反应,高产合成各种 4-取代的 2-喹啉酮化合物。这种分子间环化方法通过抑制容易发生的脱羧作用,将易得的α,β-不饱和羧酸作为偶联伙伴。基于初步的机理研究,提出了一个反应序列,包括邻位钯化、π-配位、β-迁移插入和β-氢消除。

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