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Synthesis of Functionalized 2‐Alkylidene‐tetrahydrofurans Based on a [3+2] Cyclization/Bromination/Palladium(0) Cross‐Coupling Strategy
Author(s) -
Bellur Esen,
Langer Peter
Publication year - 2005
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.200500422
Subject(s) - chemistry , halogenation , pyrrolidine , palladium , suzuki reaction , organic chemistry , coupling reaction , heck reaction , combinatorial chemistry , medicinal chemistry , catalysis
The bromination of 2‐alkylidene‐tetrahydrofurans and 2‐alkylidene‐pyrrolidines — readily available through one‐pot [3+2] cyclization reactions — afforded 2‐alkylidene‐1′‐bromotetrahydrofurans, 2‐alkylidene‐3‐bromotetrahydrofurans and 2‐alkylidene‐1′,3‐dibromotetrahydrofurans and their pyrrolidine counterparts. 2‐Alkylidene‐1′‐bromotetrahydrofurans were functionalized by performing Suzuki and Heck reactions. 2‐Alkylidene‐1′,3‐dibromotetrahydrofurans were successfully employed in novel double‐Suzuki reactions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)