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Sequential Functionalization of the OH and C( sp 2 )O Bonds of Tropolones by Alkynes and N ‐Sulfonyl Azides
Author(s) -
Seo Boram,
Jeon Woo Hyung,
Kim ChulEui,
Kim Sanghyuck,
Kim Sung Hong,
Lee Phil Ho
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500829
Subject(s) - chemistry , sulfonyl , intramolecular force , surface modification , cycloaddition , tropolone , rhodium , medicinal chemistry , catalysis , stereochemistry , organic chemistry , alkyl
Sequential copper‐catalyzed [3+2] cycloaddition, rhodium‐catalyzed OH insertion, intramolecular 1,8‐addition, and rearrangement starting from 1‐alkynes, N ‐sulfonyl azides, and tropolones is demonstrated for the synthesis of the 2‐functionalized aminotropones in one pot. These results indicate that sequential functionalization of OH and C( sp 2 )O bonds smoothly occurs in the C( sp 2 )OH bonds of tropolone