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Enabling Reductive C–N Cross-Coupling of Nitroalkanes and Boronic Acids by Steric Design of P(III)/P(V)═O Catalysts : Enabling Reductive C-N Cross-Coupling of Nitroalkanes and Boronic Acids by Steric Design of P(III)/P(V)=O Catalysts
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Cited 15 time in Scopus
- Authors
- Issue Date
- 2022-05
- Publisher
- American Chemical Society
- Citation
- Journal of the American Chemical Society, Vol.144 No.18, pp.8242-8248
- Abstract
- An organophosphorus-catalyzed C-N bond-forming reductive coupling of nitroalkanes with arylboronic acids and esters is reported. The method shows excellent chemoselectivity for the nitro/boronic acid substrate pair, allowing the synthesis of N-(hetero)arylamines rich in functionalization. The identification of a sterically reduced phosphetane catalyst capable of productive coupling in the P(III)/P(V)=O redox manifold is the key enabling development. Combined experimental kinetics and computational mechanistic studies show that the sterically reduced catalyst affects post-rate-limiting steps to enable the C-N coupling event in preference to deleterious side-paths.
- ISSN
- 0002-7863
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