Bicyclopentylation of Alcohols with Thianthrenium Reagents

被引：20

作者：

Bai, Zibo ^{[1
]}

Lansbergen, Beatrice ^{[1
]}

Ritter, Tobias ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2023年 / 145卷 / 48期

关键词：

METALLAPHOTOREDOX; ACTIVATION; CATALYSIS; RADICALS; DESIGN;

D O I：

10.1021/jacs.3c10024

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein we present the first method for the synthesis of bicyclo[1.1.1]-pentyl (BCP) alkyl ethers from alcohols. The reaction uses BCP-thianthrenium reagents and is catalyzed by a dual copper/photoredox catalyst system. Unlike known alkylations of tertiary alcohols via carbocation intermediates, our Cu-mediated radical process circumvents the labile BCP carbocations. The approach demonstrates a broad tolerance for functional groups when applied to primary, secondary, and even tertiary alcohols. In addition, we highlight the utility of this method in late-stage functionalizations of both natural products and pharmaceuticals as well as in the rapid construction of BCP analogs of known pharmaceuticals that would otherwise be difficult to access.

引用

页码：25954 / 25961

页数：8

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