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双环桥头亚磷酰胺配体和酸添加剂促进的钯催化烯丙醇与氮杂环的脱水交叉偶联反应

Palladium-Catalyzed Dehydrative Cross-Coupling of Allylic Alcohols and N-Heterocycles Promoted by a Bicyclic Bridgehead Phosphoramidite Ligand and an Acid Additive.

作者信息

Kang Kyungjun, Kim Jaewook, Lee Ansoo, Kim Woo Youn, Kim Hyunwoo

机构信息

Department of Chemistry, KAIST , Daejeon 34141, Korea.

Center for Nanomaterials and Chemical Reactions, Institute for Basic Science (IBS) , Daejeon 34141, Korea.

出版信息

Org Lett. 2016 Feb 5;18(3):616-9. doi: 10.1021/acs.orglett.6b00001. Epub 2016 Jan 13.

DOI:10.1021/acs.orglett.6b00001
PMID:26761609
Abstract

A mild and efficient dehydrative cross-coupling reaction between allylic alcohols and N-heterocycles using palladium catalysis is reported. A bicyclic bridgehead phosphoramidite (briphos) ligand together with Pd(dba)2 is a highly efficient catalyst, and an acid additive involved in the rate-determining step promotes the catalytic cycle. The coupling reaction of allylic alcohols with N-heterocycles including imidazoles, benzimidazoles, and triazole proceeds under mild reaction conditions with high yields using Pd/briphos and pentafluorophenol.

摘要

据报道,使用钯催化可实现烯丙醇与N-杂环之间温和且高效的脱水交叉偶联反应。双环桥头亚磷酰胺(briphos)配体与Pd(dba)2构成一种高效催化剂,且参与速率决定步骤的酸添加剂可促进催化循环。烯丙醇与包括咪唑、苯并咪唑和三唑在内的N-杂环的偶联反应,在温和的反应条件下,使用Pd/briphos和五氟苯酚可高产率地进行。

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