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钯配合物催化 C-H 氧化硼化实现简单烯烃的立体选择性羰基烯丙基化反应。

Diastereoselective carbonyl allylation with simple olefins enabled by palladium complex-catalyzed C-H oxidative borylation.

机构信息

Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.

出版信息

J Am Chem Soc. 2015 Apr 1;137(12):4054-7. doi: 10.1021/jacs.5b00507. Epub 2015 Mar 19.

DOI:10.1021/jacs.5b00507
PMID:25754467
Abstract

A highly diastereoselective Pd-catalyzed carbonyl allylation of aldehydes and isatins directly using simple acyclic olefins as allylating reagents is described. This transformation is actually a sequential process consisting of a Pd-catalyzed oxidative allylic C-H borylation and an allylboration of carbonyls accelerated by phosphoric acid, wherein a wide scope of olefins could be tolerated. The oxidant is revealed to play a key role in the successful realization of the allylic C-H activation-based allylation.

摘要

本文描述了一种高非对映选择性的钯催化羰基烯丙基化反应,可直接使用简单的非环烯烃作为烯丙基化试剂。该转化实际上是一个由钯催化氧化烯丙基 C-H 硼化和磷酸加速的羰基烯丙基化组成的连续过程,其中可以容忍广泛范围的烯烃。氧化剂被证明在成功实现基于烯丙基 C-H 活化的烯丙基化中起着关键作用。

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