One‐Pot Approach to Installing Eight‐Membered Rings onto Indoles | Zendy

Zhu Can | Zendy; Zhang Xue | Zendy; Lian Xiongdong | Zendy; Ma Shengming | Zendy

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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.

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