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One‐Pot Approach to Installing Eight‐Membered Rings onto Indoles
Author(s) -
Zhu Can,
Zhang Xue,
Lian Xiongdong,
Ma Shengming
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.201202971
Subject(s) - phosphine , ring (chemistry) , chemistry , tosyl , combinatorial chemistry , tris , molecular sieve , medicinal chemistry , annulation , organic chemistry , catalysis , biochemistry
Ring fusion : The Pd 0 ‐catalyzed reaction of 2‐allyl‐3‐iodo‐1‐tosyl‐1 H ‐indoles and propargylic bromides affords dihydrocycloocta[ b ]indoles (see scheme; M.S.=molecular sieves, TFP=tris(2‐furyl)phosphine, Ts=4‐toluenemethanesulfonyl), and proceeds by carbon–carbon coupling, [1,5]‐hydrogen migration, and electrocyclization. The newly established method was used to efficiently access iprindole.