Journal
CHEMICAL SCIENCE
Volume 6, Issue 3, Pages 1917-1922Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4sc03337j
Keywords
-
Categories
Funding
- National Science Foundation under the CCI Center for Selective C-H Functionalization [CHE-1205646]
- Center for Molecular Analysis and Design (CMAD) at Stanford University
- University of Utah [10029173-S2]
- Air Force Office of Scientific Research [FA9550-12-1-0481]
- Caltech
- Amgen
- American Chemical Society Division of Organic Chemistry
- National Institutes of Health [F32GM106596]
- NSF
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1205646] Funding Source: National Science Foundation
Ask authors/readers for more resources
An asymmetric palladium-catalyzed conjugate addition reaction of arylboronic acids to enone substrates was investigated mechanistically. Desorption electrospray ionization coupled to mass spectrometry was used to identify intermediates of the catalytic cycle and delineate differences in substrate reactivity. Our findings provide evidence for the catalytic cycle proceeding through formation of an arylpalladium(II) cation, subsequent formation of an arylpalladium-enone complex, and, ultimately, formation of the new C-C bond. Reaction monitoring in both positive and negative ion modes revealed that 4-iodophenylboronic acid formed a relatively stable trimeric species under the reaction conditions.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available