Unprecedented Intra‐ and Intermolecular Palladium‐Catalyzed Coupling Reactions with Methylenecylclopropane‐Type Tetrasubstituted Alkenes | Zendy

Bräse Stefan | Zendy; de Meijere Armin | Zendy

Premium

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research