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Direct Synthesis of Substituted ( Z )‐Allylic Sulfones by Palladium‐Catalyzed Sulfonylation of Vinylethylene Carbonates with Sodium Sulfinates
Author(s) -
Ke Miaolin,
Huang Guanxin,
Ding Li,
Fang Jingjie,
Chen Fener
Publication year - 2019
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201901292
Subject(s) - allylic rearrangement , stereoselectivity , palladium , sulfone , chemistry , regioselectivity , sulfonyl , catalysis , sodium , medicinal chemistry , organic chemistry , alkyl
A palladium‐catalyzed highly stereoselective sulfonylation of vinylethylene carbonates for the precise synthesis of structurally diverse ( Z )‐allylic sulfones was achieved with excellent regioselectivity and stereoselectivity ( Z / E ratio, up to 99 : 1). This protocol used inexpensive sodium sulfinates as sulfonyl sources to construct valuable ( Z )‐allylic sulfones in good to excellent yields. The controlling experiment suggested that the hydroxyl proton came from the α‐hydrogen of sulfone group through 1, 5‐H shift.