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Solution-phase synthesis of a highly substituted furan library.

ABSTRACT: A library of furans has been synthesized by iodocyclization and further diversified by palladium-catalyzed coupling processes. The key intermediate 3-iodofurans have been prepared by the electrophilic iodocyclization of 2-iodo-2-alken-1-ones in the presence of various nucleophiles in good to excellent yields under mild reaction conditions. These 3-iodofurans are the key components for library generation through subsequent elaboration by palladium-catalyzed processes, such as Suzuki-Miyaura, Sonagashira, Heck, aminocarbonylation, and carboalkoxylation chemistry to afford a diverse set of 2,3,4,5-tetrasubstituted furans.

SUBMITTER: Cho CH

PROVIDER: S-EPMC3437248 | biostudies-literature | 2012 Jul

REPOSITORIES: biostudies-literature

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Solution-phase synthesis of a highly substituted furan library.

Cho Chul-Hee CH Shi Feng F Jung Dai-Il DI Neuenswander Benjamin B Lushington Gerald H GH Larock Richard C RC

ACS combinatorial science 20120611 7

A library of furans has been synthesized by iodocyclization and further diversified by palladium-catalyzed coupling processes. The key intermediate 3-iodofurans have been prepared by the electrophilic iodocyclization of 2-iodo-2-alken-1-ones in the presence of various nucleophiles in good to excellent yields under mild reaction conditions. These 3-iodofurans are the key components for library generation through subsequent elaboration by palladium-catalyzed processes, such as Suzuki-Miyaura, Sona ...[more]

PMID: 22612549

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