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General method for functionalized polyaryl synthesis via aryne intermediates.

ABSTRACT: A method for base-promoted arylation of arenes and heterocycles by aryl halides and aryl triflates is described. Additionally, in situ electrophilic trapping of ArLi intermediates generated in the reaction of benzyne with deprotonated arenes or heterocycles has been developed, providing rapid and easy access to a wide range of highly functionalized polyaryls. Base-promoted arylation methodology complements transition-metal-catalyzed direct arylation and allows access to structures that are not easily accessible via other direct arylation methods. The reactions are highly functional-group tolerant, with alkene, ether, dimethylamino, trifluoromethyl, ester, cyano, halide, hydroxyl, and silyl functionalities compatible with reaction conditions.

SUBMITTER: Truong T

PROVIDER: S-EPMC4227807 | biostudies-other | 2014 Jun

REPOSITORIES: biostudies-other

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General method for functionalized polyaryl synthesis via aryne intermediates.

Truong Thanh T Mesgar Milad M Le Ky Khac Anh KK Daugulis Olafs O

Journal of the American Chemical Society 20140603 24

A method for base-promoted arylation of arenes and heterocycles by aryl halides and aryl triflates is described. Additionally, in situ electrophilic trapping of ArLi intermediates generated in the reaction of benzyne with deprotonated arenes or heterocycles has been developed, providing rapid and easy access to a wide range of highly functionalized polyaryls. Base-promoted arylation methodology complements transition-metal-catalyzed direct arylation and allows access to structures that are not e ...[more]

PMID: 24893069

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