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Divergent Reactions between α‐Imino Rhodium Carbenoids and 1,3‐Diketones: Substrate‐Controlled O–H versus C–H Insertion
Author(s) -
Mi Pengbing,
Yuan Haiyan,
Wang Hannan,
Liao Peiqiu,
Zhang Jingping,
Bi Xihe
Publication year - 2017
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.201700009
Subject(s) - chemistry , rhodium , insertion reaction , diketone , substrate (aquarium) , pyrrole , sulfonyl , medicinal chemistry , condensation reaction , stereochemistry , catalysis , organic chemistry , oceanography , alkyl , geology
The cyclization reaction between N ‐sulfonyl‐1,2,3‐triazoles and 1,3‐diketones was explored. This reaction provides a new and powerful method for the synthesis of highly functionalized pyrroles and fused pyrrole derivatives. Mechanistically, the reaction was found to proceed through tandem O–H or C–H insertion/condensation of in situ generated α‐imino rhodium carbenoids with 1,3‐diketones. The initial O–H or C–H insertion was determined to be dependent on the type of 1,3‐diketone.