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Double heteroatom functionalization of arenes using benzyne three-component coupling.

ABSTRACT: Arynes participate in three-component coupling reactions with N, S, P, and Se functionalities to yield 1,2-heteroatom-difunctionalized arenes. Using 2-iodophenyl arylsulfonates as benzyne precursors, we could effectively add magnesiated S-, Se-, and N-nucleophilic components to the strained triple bond. In the same pot, addition of electrophilic N, S, or P reagents and a copper(I) catalyst trapped the intermediate aryl Grignard to produce a variety of 1,2-difunctionalized arenes.

SUBMITTER: Garcia-Lopez JA

PROVIDER: S-EPMC4832838 | biostudies-other | 2015 Feb

REPOSITORIES: biostudies-other

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Double heteroatom functionalization of arenes using benzyne three-component coupling.

García-López José-Antonio JA Çetin Meliha M Greaney Michael F MF

Angewandte Chemie (International ed. in English) 20150107 7

Arynes participate in three-component coupling reactions with N, S, P, and Se functionalities to yield 1,2-heteroatom-difunctionalized arenes. Using 2-iodophenyl arylsulfonates as benzyne precursors, we could effectively add magnesiated S-, Se-, and N-nucleophilic components to the strained triple bond. In the same pot, addition of electrophilic N, S, or P reagents and a copper(I) catalyst trapped the intermediate aryl Grignard to produce a variety of 1,2-difunctionalized arenes. ...[more]

PMID: 25580700

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