The vinylogous Catellani reaction: a combined computational and experimental study

In the presence of 5 mol% Pd(OAc)(2), 1 equiv. of norbornene, and K2CO3, 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 bas...

Full description

Saved in:
Bibliographic Details
Published inChemical science (Cambridge) Vol. 9; no. 5; pp. 1191 - 1199
Main Authors Yamamoto, Y., Murayama, T., Jiang, J., Yasui, T., Shibuya, M.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2018
Royal Society of Chemistry
Subjects
Alcohols
Chemistry
Chemistry, Multidisciplinary
Density functional theory
Physical Sciences
Science & Technology
CATALYSIS
ACTIVATION
FERULA-COMMUNIS
HETEROCYCLES
MECHANISM
ARYLATION
C-H FUNCTIONALIZATION
PD/NORBORNENE
FERPRENIN
ALKALOIDS
Online AccessGet full text

Cover

More Information
Summary:In the presence of 5 mol% Pd(OAc)(2), 1 equiv. of norbornene, and K2CO3, 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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:2041-6520
2041-6539
DOI:10.1039/c7sc04265e