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• W2891465206 abstract "We report herein on the synthesis of new heteroaryl analogues of PAd-DalPhos and related bis(di(o-tolyl)phosphino) ancillary ligand variants based on pyridine or thiophene backbone structures, and their application in nickel-catalyzed C(sp2)-N cross-couplings under challenging reaction conditions. The 3,4-disubstituted thiophene-based ancillary ligand ThioPAd-DalPhos (L8) was observed to be particularly effective in the nickel-catalyzed C(sp2)-N cross-coupling of primary alkylamines, and the derived precatalyst (L8)NiCl(o-tolyl) (C2) was found to offer improved performance versus the related PAd-DalPhos-derived precatalyst C1 in such transformations. In using C2, cross-couplings of various primary alkylamines and (hetero)aryl-X electrophiles (X = Cl, Br, OTs) proceeded under unprecedentedly mild reaction conditions (0.25–0.50 mol % Ni), including examples conducted at room temperature. Also reported herein are the results of our combined experimental/DFT computational study directed toward gaining insight regarding the improved catalytic performance of C2 versus C1." @default.
• W2891465206 created "2018-09-27" @default.
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• W2891465206 date "2018-09-14" @default.
• W2891465206 modified "2023-10-13" @default.
• W2891465206 title "Examining the Impact of Heteroaryl Variants of PAd-DalPhos on Nickel-Catalyzed C(<i>sp</i>²)-N Cross-Couplings" @default.
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• W2891465206 doi "https://doi.org/10.1021/acs.organomet.8b00451" @default.
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