Journal
CHEMCATCHEM
Volume -, Issue -, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.202300412
Keywords
Renewable alcohols; Alkyl alcohols; non-precious catalysis; Nickel; Hydrogen-borrowing; C-3 substututed quinolines
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In this study, a general and efficient Ni-catalyzed protocol for sequential double de-hydrogenative cyclization was reported, which can convert 2-amino(nitro)-benzyl alcohols with primary alcohols to C-3-substituted quinolines, releasing water and dihydrogen as byproducts. The late stage functionalization of cholesterol derivatives, including chemo-selective transformations of citronellol, fatty acid derived oleyl alcohol, and long chain C-4-C-14 alkyl alcohols, was highlighted. Initial mechanistic studies, including deuterium-labelling experiments, were conducted to establish the de-hydrogenative cyclization.
We herein reported a general and efficient Ni-catalyzed protocol for sequential double de-hydrogenative cyclization of 2-amino(nitro)-benzyl alcohols with primary alcohols to C-3-substituted quinolines releasing water and dihydrogen as by products. As a special highlight, late stage functionalization of cholesterol derivative including chemo-selective transformations of citronellol, fatty acid derived oleyl alcohol and long chain C-4-C-14 alkyl alcohols were reported. Initial mechanistic studies including deuterium-labelling experiments were perform to establish the de-hydrogenative cyclization.
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