Journal
CHEMICAL RECORD
Volume 11, Issue 5, Pages 242-251Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/tcr.201100023
Keywords
alkynes; C-H functionalization; hydroarylation; Lewis acids; nickel
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Funding
- MEXT [16GS0209, 21225005, 19028030, 20037035, 22105003]
- JSPS
- Grants-in-Aid for Scientific Research [19028030, 22105003, 20037035, 16GS0209] Funding Source: KAKEN
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Nickel catalysts derived from bis(1,5-cyclooctadiene) nickel [ Ni(cod)(2)] and trialkylphosphines effect hydroarylation of alkynes through functionalization of C-H bonds of arenes including benzo-fused five-membered heteroarenes, pyridine-N-oxides, pyridines, 2-pyridones, and perfluoroarenes. The reactions proceed with excellent stereo-and regioselectivity to give disubstituted arylethenes in good yields. Use of Lewis acid (LA) co-catalysts is crucial for success in reactions of imidazoles, pyridines, and 2-pyridones; it is possible that coordination of the LA to the nitrogen or oxygen functionalities of such substrates increases the reactivity of their C-H bonds towards nickel(0) species. DOI 10.1002/tcr.201100023
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