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Gold‐Catalyzed Chemoselective Synthesis of Heterocycles from 3‐(2‐Azidophenyl)prop‐2‐yn‐1‐ols and Aldehydes
Author(s) -
Zhang Xiaoxiang,
Sun Xiaoping,
Fan Hui,
Li Ping,
Lyu Chang,
Rao Weidong
Publication year - 2016
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.201600789
Subject(s) - chemistry , chemoselectivity , annulation , catalysis , imide , tandem , organic chemistry , medicinal chemistry , reaction conditions , aldehyde , combinatorial chemistry , materials science , composite material
An efficient method to prepare 6‐(2‐azidophenyl)‐4 H ‐1,3‐dioxins and 4,5‐dihydro[1,3]dioxino[5,4‐ b ]indoles by gold‐catalyzed tandem‐annulation of 3‐(2‐azidophenyl)prop‐2‐yn‐1‐ols with aldehydes was examined. The reactions afforded the products in moderate to excellent yields under mild reaction conditions. Uniquely, the reactions proceeded with complete control of product chemoselectivity for a variety of 3‐(2‐azidophenyl)prop‐2‐yn‐1‐ols in the presence of 2‐dicyclohexylphosphino‐2′,4′,6′‐triisopropylbiphenylgold(I) bis(trifluoromethanesulfonyl)imide (XPhosAuNTf 2 ).