Ni-catalyzed deaminative cross-electrophile coupling of Katritzky salts with halides via C─N bond activation

Science Advances, Journal Year: 2019, Volume and Issue: 5(6)

Published: June 1, 2019

Reductive cross-coupling of primary amines and alkyl halides goes through a radical change.

Language: Английский

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Metal-catalysed C–Het (F, O, S, N) and C–C bond arylation

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(16), P. 8903 - 8953

Published: Jan. 1, 2021

The formation of C–aryl bonds has been the focus intensive research over last decades for construction complex molecules from simple, readily available feedstocks.

Language: Английский

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Decarbonylative Phosphorylation of Amides by Palladium and Nickel Catalysis: The Hirao Cross‐Coupling of Amide Derivatives

Angewandte Chemie International Edition, Journal Year: 2017, Volume and Issue: 56(41), P. 12718 - 12722

Published: Aug. 15, 2017

Abstract Considering the ubiquity of organophosphorus compounds in organic synthesis, pharmaceutical discovery agrochemical crop protection and materials chemistry, new methods for their construction hold particular significance. A conventional method synthesis C−P bonds involves cross‐coupling aryl halides dialkyl phosphites (the Hirao reaction). We report a catalytic deamidative phosphorylation wide range amides using palladium or nickel catalyst giving phosphonates good to excellent yields. The present tolerates functional groups. reaction constitutes first example transition‐metal‐catalyzed generation from amides. This redox‐neutral protocol can be combined with site‐selective regioselective potential pharmacophores. Mechanistic studies suggest an oxidative addition/transmetallation pathway. In light importance as synthetic intermediates, we envision that this Pd Ni‐catalyzed bond forming will find broad application.

Language: Английский

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General Method for the Suzuki–Miyaura Cross-Coupling of Amides Using Commercially Available, Air- and Moisture-Stable Palladium/NHC (NHC =N-Heterocyclic Carbene) Complexes

ACS Catalysis, Journal Year: 2017, Volume and Issue: 7(3), P. 1960 - 1965

Published: Feb. 13, 2017

The direct Suzuki–Miyaura cross-coupling of amides catalyzed by Pd-NHC complexes is reported. Using a single protocol, commercially available, air- and moisture-stable (NHC)Pd(R-allyl)Cl can effect wide range with arylboronic acids in very good yields. studies described herein represent the use versatile as catalysts for transition-metal-catalyzed N–C bond activation. provide significant improvement over all current Pd-PR3 systems employed amide Mechanistic strong support development unified reactivity scale generation acyl-metal intermediates.

Language: Английский

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Pd–PEPPSI: a general Pd–NHC precatalyst for Buchwald–Hartwig cross-coupling of esters and amides (transamidation) under the same reaction conditions

Chemical Communications, Journal Year: 2017, Volume and Issue: 53(76), P. 10584 - 10587

Published: Jan. 1, 2017

We report the first catalytic Buchwald–Hartwig amination of both common esters and amides by highly selective C(acyl)–X cleavage using well-defined Pd–PEPPSI type precatalysts.

Language: Английский

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