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Reciprocal-Activation Strategy for Allylic Sulfination with Unactivated Allylic Alcohols

Peizhong Xie, Zuolian Sun, Shuangshuang Li, Xinying Cai, Ju Qiu, Weishan Fu, Cuiqing Gao, WU Shi-sheng, Xiaobo Yang, Teck‐Peng Loh

2020Organic Letters32 citationsDOI

Abstract

A reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols was developed. In this reaction, the hydrogen bond interaction between allylic alcohols and sulfinic acids allowed for reciprocal activation, which enabled a dehydrative cross-coupling process to occur under mild reaction conditions. This reaction worked in an environmentally friendly manner, yielding water as the only byproduct. A variety of allylic sulfones could be obtained in good to excellent yields with wide functional group tolerance. In gram scale reactions, allylic sulfones could be conveniently isolated in high yield by filtration.

Topics & Concepts

Allylic rearrangementChemistryYield (engineering)Functional groupCatalysisOrganic chemistryCombinatorial chemistryMaterials scienceMetallurgyPolymerSulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsCatalytic C–H Functionalization Methods
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