NDLI: Selective base-promoted synthesis of substituted selenophenes by carbocyclization of (Z)-benzylselenoenynes

Content Provider	Royal Society of Chemistry (RSC)
Author	Barancelli, Daniela A. Acker, Carmine I. Zeni, Gilson Menezes, Paulo H.
Copyright Year	2011
Abstract	We herein described the synthesis of several 3-benzyl-2,5-diarylselenophene derivatives in moderate to good yields using (Z)-benzylselenoenynes as starting material in carbocyclization reactions. The reactions were carried out under mild conditions using only t-BuOK as base, in the complete absence of transition metals or additives. The cyclized 3-benzyl-2,5-diarylselenophenes obtained in the current protocol appear highly promising and attractive intermediates for the synthesis of polysubstituted selenophenes. For instance, 3-benzyl-2,5-diphenylselenophene was treated with Br2 provided the corresponding 3-benzyl-4-bromo-2,5-diphenylselenophene in high yield. 4-Bromoselenophene derivative was applied as substrate in the palladium catalyzed cross-coupling reactions with boronic acids to give the Suzuki type products in excellent yields.
Starting Page	1529
Ending Page	1537
Page Count	9
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	9
Issue Number	5
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/c0ob00844c
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Bromine Potassium tert-butoxide Suzuki Benzyl group Suzuki reaction
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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Selective base-promoted synthesis of substituted selenophenes by carbocyclization of (Z)-benzylselenoenynes