Tetrahedron p. 437 - 452 (1994)
Update date:2022-09-26
Topics:
Arcadi
Cacchi
Carnicelli
Marinelli
The palladium-catalysed reaction of readily accessible 2- alkynyltrifluoroacetanilides with aryl halides and vinyl triflates under a carbon monoxide atmosphere (1 or 7 atm) and in the presence of potassium carbonate produces 2-substituted-3-acyl indoles in fair to good yield. The acidity of the nitrogen-hydrogen bond proved to be of primary importance for the success of the reaction. The methodology has been applied to the synthesis of pravadoline, a drug that shows analgesic activity against postoperative pain in man.
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Doi:10.1021/jo00084a009
(1994)Doi:10.1248/cpb.41.961
(1993)Doi:10.1016/0022-1139(93)02893-J
(1994)Doi:10.1016/0040-4039(94)88517-6
(1994)Doi:10.1021/om401208y
(2014)Doi:10.1002/cjoc.201400413
(2014)
