Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Synthesis of 3-Arylbenzofuran-2-ylphosphines via Rhodium-Catalyzed Redox-Neutral C–H Activation and Their Applications in Palladium-Catalyzed Cross-Coupling of Aryl Chlorides

Synthesis of 3-Arylbenzofuran-2-ylphosphines via Rhodium-Catalyzed Redox-Neutral C–H Activation and Their Applications in Palladium-Catalyzed Cross-Coupling of Aryl Chlorides
Baiquan Wang, Bin Li, Huanan Wang
A new class of aryl-heteroarylphosphines, 3-arylbenzofuran-2-ylphosphines, was synthesized by [Cp*Rh(III)]-catalyzed redox-neutral cyclization of N-phenoxyacetamides with 1-alkynylphosphine sulfides and oxides followed by reduction. This step-economic reaction proceeds in excellent regioselectivity with a broad substrate scope. The application of the resulting air-stable trivalent-phosphine containing dicyclohexylphosphino moiety in palladium-catalyzed Suzuki–Miyaura coupling and Buchwald–Hartwig amination of aryl chlorides is also described.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01566

DOI: 10.1021/acs.joc.7b01566

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