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Sodium Arenesulfinates‐Involved Sulfinate Synthesis Revisited: Improved Synthesis and Revised Reaction Mechanism
Author(s) -
Ji YuanZhao,
Li HuiJing,
Zhang JinYu,
Wu YanChao
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900097
Subject(s) - chemistry , carbocation , sulfone , reaction mechanism , mechanism (biology) , combinatorial chemistry , substrate (aquarium) , organic chemistry , catalysis , geology , philosophy , oceanography , epistemology
Reaction of alcohols with sodium arenesulfinates could afford either sulfones or sulfinates, and O‐attack of sulfinate anions onto the in situ generated carbocation intermediates from alcohols was the previous proposed reaction mechanism in many syntheses of sulfinates. This concept, which is often used consciously or unconsciously, was revised herein by using isotopic labeling experiments and development of an improved sulfinate synthesis. The improved sulfinate synthetic protocol possesses many advantages such as a high sulfinate/sulfone selectivity, a broad substrate scope, metal‐free, and mild reaction conditions. The revised reaction mechanism necessitates revision of many previous proposed reaction mechanisms in literatures.