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Unprecedented Intra‐ and Intermolecular Palladium‐Catalyzed Coupling Reactions with Methylenecylclopropane‐Type Tetrasubstituted Alkenes
Author(s) -
Bräse Stefan,
de Meijere Armin
Publication year - 1995
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199525451
Subject(s) - palladium , alkene , chemistry , catalysis , heck reaction , coupling reaction , intermolecular force , domino , cascade reaction , ring (chemistry) , medicinal chemistry , cascade , coupling (piping) , photochemistry , polymer chemistry , organic chemistry , materials science , molecule , chromatography , metallurgy
A reaction cascade consisting of a Heck coupling, cyclopropyl ring‐opening, and a domino Diels–Alder reaction proceeds in one pot. The palladium‐catalyzed coupling of bicyclopylidene ( 1 ) with vinyl iodide, even in the presence of dienophile 3 , affords dendralene 2 , which then reacts smoothly with 3 (R 1 = H, CO 2 Me; R 2 = CO 2 Me) to give bisadducts 4 in satisfactory yields. The key factor in this reaction sequence is that the carbopalladation of the unusual tetrasubstituted alkene 1 proceeds more rapidly than the Heck reaction with the dienophile.