Cyclic carbopalladation of alkynes terminated by carbonylative amidation

Termination of cyclic carbopalladation of alkynes via carbonylative lactamization can be achieved more satisfactorily with alkenyl or aryl halides containing an ω-sulfonamido group than with those containing an ω-amino group. The method appears to be generally satisfactory for the preparation of fus...

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Bibliographic Details
Published inTetrahedron Vol. 52; no. 35; pp. 11529 - 11544
Main Authors Copéret, Christophe, Ma, Shengming, Sugihara, Takumichi, Negishi, Ei-ichi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 26.08.1996
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HALIDES
METAL-PROMOTED CYCLIZATION
ALKENES
ROUTE
BENZENE
PALLADIUM-CATALYZED AMIDATION
CASCADE
ANION CAPTURE PROCESSES
DERIVATIVES
CARBOMETALATION
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ISSN0040-4020
1464-5416
DOI10.1016/0040-4020(96)00640-0

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Summary:Termination of cyclic carbopalladation of alkynes via carbonylative lactamization can be achieved more satisfactorily with alkenyl or aryl halides containing an ω-sulfonamido group than with those containing an ω-amino group. The method appears to be generally satisfactory for the preparation of fused cyclic systems consisting of six-membered rings, while the other cases require further development. Intramolecular lactamization of acylpalladium derivatives with internal carboxamides and sulfonamides and its application to the development of cyclic carbopalladation-carbonylative lactamization cascades
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(96)00640-0