TY - JOUR
T1 - Chemo- and regioselective cyclohydrocarbonylation of α-keto alkynes catalyzed by a zwitterionic rhodium complex and triphenyl phosphite
AU - Van den Hoven, B. G.
AU - El Ali, B.
AU - Alper, H.
PY - 2000/6/30
Y1 - 2000/6/30
N2 - α-Keto alkynes react with CO and H2 in the presence of catalytic quantities of the zwitterionic rhodium complex (η6-C6H5BPh3)- Rh+(1,5-COD) and triphenyl phosphite affording either the 2-, 2(3H)-, or 2(5H)-furanones in 61-93% yields. The cyclohydrocarbonylation is readily accomplished using substrates containing alkyl, aryl, vinyl, and alkoxy groups at the acetylenic terminal, as well as a variety of primary, secondary, and tertiary alkyl, aryl, and heteroaryl groups connected to the ketone functionality. Structural and electronic properties present in the starting materials mediate the chemo- and regioselectivity of the reaction.
AB - α-Keto alkynes react with CO and H2 in the presence of catalytic quantities of the zwitterionic rhodium complex (η6-C6H5BPh3)- Rh+(1,5-COD) and triphenyl phosphite affording either the 2-, 2(3H)-, or 2(5H)-furanones in 61-93% yields. The cyclohydrocarbonylation is readily accomplished using substrates containing alkyl, aryl, vinyl, and alkoxy groups at the acetylenic terminal, as well as a variety of primary, secondary, and tertiary alkyl, aryl, and heteroaryl groups connected to the ketone functionality. Structural and electronic properties present in the starting materials mediate the chemo- and regioselectivity of the reaction.
UR - https://www.scopus.com/pages/publications/0034733129
U2 - 10.1021/jo000230w
DO - 10.1021/jo000230w
M3 - Article
AN - SCOPUS:0034733129
SN - 0022-3263
VL - 65
SP - 4131
EP - 4137
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 13
ER -