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SO 2 F 2 ‐Activated Efficient Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams
Author(s) -
Zhang Guofu,
Zhao Yiyong,
Xuan Lidi,
Ding Chengrong
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.201900844
Subject(s) - beckmann rearrangement , chemistry , yield (engineering) , substrate (aquarium) , combinatorial chemistry , scope (computer science) , medicinal chemistry , stereochemistry , computational chemistry , organic chemistry , catalysis , materials science , oceanography , computer science , metallurgy , programming language , geology
A novel, mild and practical protocol for the efficient activation of the Beckmann rearrangement utilizing the readily available and economical sulfuryl fluoride (SO 2 F 2 gas) has been developed. The substrate scope of the operationally simple methodology has been demonstrated by 37 examples with good to nearly quantitative isolated yields (over 90 % yield in most cases) in a short time, including B(OH) 2 , COOH, NH 2 , and OH substituted substrates. A tentative mechanism was proposed involving formation and elimination of key intermediate, sulfonyl ester.