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Intermolecular Reductive C-N Cross Coupling of Nitroarenes and Boronic Acids by PIII/PV?O Catalysis.

ABSTRACT: A main group-catalyzed method for the synthesis of aryl- and heteroarylamines by intermolecular C-N coupling is reported. The method employs a small-ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane) and a terminal hydrosilane reductant (phenylsilane) to drive reductive intermolecular coupling of nitro(hetero)arenes with boronic acids. Applications to the construction of both Csp2-N (from arylboronic acids) and Csp3-N bonds (from alkylboronic acids) are demonstrated; the reaction is stereospecific with respect to Csp3-N bond formation. The method constitutes a new route from readily available building blocks to valuable nitrogen-containing products with complementarity in both scope and chemoselectivity to existing catalytic C-N coupling methods.

SUBMITTER: Nykaza TV

PROVIDER: S-EPMC6235741 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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Intermolecular Reductive C-N Cross Coupling of Nitroarenes and Boronic Acids by PIII/PV═O Catalysis.

Nykaza Trevor V TV Cooper Julian C JC Li Gen G Mahieu Nolwenn N Ramirez Antonio A Luzung Michael R MR Radosevich Alexander T AT

Journal of the American Chemical Society 20181102 45

A main group-catalyzed method for the synthesis of aryl- and heteroarylamines by intermolecular C-N coupling is reported. The method employs a small-ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane) and a terminal hydrosilane reductant (phenylsilane) to drive reductive intermolecular coupling of nitro(hetero)arenes with boronic acids. Applications to the construction of both Csp2-N (from arylboronic acids) and Csp3-N bonds (from alkylboronic acids) ar ...[more]

PMID: 30372615

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