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Room Temperature Nickel(0)‐Catalyzed Suzuki–Miyaura Cross‐Couplings of Activated Alkenyl Tosylates: Efficient Synthesis of 4‐Substituted Coumarins and 4‐Substituted 2( 5H )‐ Furanones
Author(s) -
Tang ZhenYu,
Hu QiaoSheng
Publication year - 2004
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.200404150
Subject(s) - chemistry , tricyclohexylphosphine , catalysis , aryl , nickel , organic chemistry , combinatorial chemistry , medicinal chemistry , phosphine , alkyl
Abstract Room temperature nickel(0)/tricyclohexylphosphine [Ni(0)/PCy 3 ]‐catalyzed Suzuki–Miyaura cross‐couplings of 4‐( p ‐toluenesulfonyloxy)coumarins and 4‐( p ‐toluenesulfonyloxy)‐2( 5H )‐furanone with arylboronic acids are described in this communcation. Our study shows that activated alkenyl tosylates possess higher activities than aryl tosylates in the Suzuki–Miyaura cross‐couplings. The mild reaction conditions and the high efficiency of the Ni(0)/PCy 3 catalyst make it very useful in the synthesis of 4‐substituted coumarins and 4‐substituted 2( 5H )‐furanones, two families of biologically important molecules.