The vinylogous Catellani reaction: a combined computational and experimental study. Issue 5 (15th December 2017)

• Record Type: Journal Article
• Authors: Yamamoto, Y.; Murayama, T.; Jiang, J.; Yasui, T.; Shibuya, M.
• Is Part Of: Chemical science. Volume 9:Issue 5(2018)
• Page Start: 1191
• Page End: 1199
• Publication Date: 2017-12-15
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c7sc04265e
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : In the presence of 5 mol% Pd(OAc)2, 1 equiv. of norbornene, and K2 CO3, the reaction of 4-iodo-2-quinolones with tertiary o -bromobenzylic alcohols produced the desired benzopyran-fused 2-quinolones in moderate to high yields. Abstract : In the presence of 5 mol% Pd(OAc)2, 1 equiv. of norbornene, and K2 CO3, the reaction of 4-iodo-2-quinolones with tertiary o -bromobenzylic alcohols produced the desired benzopyran-fused 2-quinolones in moderate to high yields. A Catellani-type mechanism involving vinylic C–H cleavage is proposed based on the results of control experiments and density functional theory calculations.