Journal
CHEMSUSCHEM
Volume 11, Issue 22, Pages 3911-3916Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.201801443
Keywords
amides; alkylation; homogeneous catalysis; hydrogen transfer; nickel
Funding
- SERB-Green Chemistry programme [EMR/2015/000030]
- CSIR-INPROTICS PA [HCP0011A]
- CSIR
- SERB [EMR/2016/006106]
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A transition-metal-catalyzed borrowing hydrogen/hydrogen auto-transfer strategy allows the utilization of feedstock alcohols as an alkylating partner, which avoids the formation of stoichiometric salt waste and enables a direct and benign approach for the construction of C-N and C-C bonds. In this study, a nickel-catalyzed alpha-alkylation of unactivated amides and ester (tert-butyl acetate) is carried out by using primary alcohols under mild conditions. This C-C bond-forming reaction is catalyzed by a new, molecularly defined nickel(II) NNN-pincer complex (0.1-1 mol %) and proceeds through hydrogen auto-transfer, thereby releasing water as the sole byproduct. In addition, N-alkylation of cyclic amides under Ni-catalytic conditions is demonstrated.
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