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Ring Expansion and Rearrangements of Rhodium(II) Azavinyl Carbenes
Author(s) -
Selander Nicklas,
Worrell Brady T.,
Fokin Valery V.
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201207820
Subject(s) - regioselectivity , rhodium , sulfonyl , olefin fiber , chemistry , ring (chemistry) , ketone , catalysis , combinatorial chemistry , medicinal chemistry , organic chemistry , alkyl
Room for expansion : An efficient, regioselective, and convergent method for the ring expansion and rearrangement of 1‐sulfonyl‐1,2,3‐triazoles under rhodium(II)‐catalyzed conditions is described. These denitrogenative reactions form substituted enaminone and olefin‐based products (see scheme). The enaminone products can be further functionalized to give various heterocycles and ketone derivatives, thus rendering the sulfonyl triazole traceless.