铜催化的位点选择性苄基氯化反应实现与氧化敏感亲核试剂的净碳氢键偶联
Cu-Catalyzed Site-Selective Benzylic Chlorination Enabling Net C-H Coupling with Oxidatively Sensitive Nucleophiles.
作者信息
Lopez Marco A, Buss Joshua A, Stahl Shannon S
机构信息
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.
出版信息
Org Lett. 2022 Jan 21;24(2):597-601. doi: 10.1021/acs.orglett.1c04038. Epub 2021 Dec 29.
Abstract
Site-selective chlorination of benzylic C-H bonds is achieved using a CuCl/bis(oxazoline) catalyst with -fluorobenzenesulfonimide as the oxidant and KCl as a chloride source. This method exhibits higher benzylic selectivity, relative to established chlorination protocols, and is compatible with diverse alkyl arenes. Sequential benzylic C-H chlorination/nucleophilic substitution affords C-O, C-S, and C-N coupling products with oxidatively sensitive coupling partners.
摘要
使用氯化铜/双（恶唑啉）催化剂，以-氟苯磺酰亚胺作为氧化剂，氯化钾作为氯源，实现了苄基C-H键的位点选择性氯化。相对于已有的氯化方法，该方法具有更高的苄基选择性，并且与多种烷基芳烃兼容。苄基C-H氯化/亲核取代反应序列可与对氧化敏感的偶联伙伴生成C-O、C-S和C-N偶联产物。
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