Calcium-catalyzed carboarylation of alkynes.
The first transition-metal-free carboarylation of alkynes with commercial and readily available alcohols as alkylating agents was realized in the presence of an environmentally benign calcium catalyst. Thereby, a novel protocol for the one-step synthesis of highly congested, all-carbon tetrasubstituted alkenes, as incorporated in potentially bioactive, complex dihydronaphthalene, chromene and dihydroquinoline structures, is provided. The reaction features an unprecedented, particularly wide substrate scope, good functional-group tolerance and simple experimental operation under mild reaction conditions.
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany) http://www.ioc.rwth-aachen.de.
Liang
L
Fu
Meike
M
Niggemann
D000438:Alcohols / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D001578:Benzopyrans / Q000737:chemistry; D002118:Calcium / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry; D011804:Quinolines / Q000737:chemistry; D013237:Stereoisomerism
D000438:Alcohols; D000475:Alkenes; D000480:Alkynes; D001578:Benzopyrans; D009281:Naphthalenes; D011804:Quinolines; D002118:Calcium
alkynes; calcium; carboarylation; synthetic methods; tetrasubstituted alkenes