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J Am Chem Soc. 2017 Dec 27;139(51):18500-18503. doi: 10.1021/jacs.7b11962. Epub 2017 Dec 14.

Dynamic Ligand Exchange as a Mechanistic Probe in Pd-Catalyzed Enantioselective C-H Functionalization Reactions Using Monoprotected Amino Acid Ligands.

Author information

1
Department of Chemistry, The Scripps Research Institute , La Jolla, California 92037, United States.
2
Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095, United States.
3
Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University , Nagoya 464-8602, Japan.

Abstract

A new tool for probing enantioselective reaction mechanisms is introduced. Monitoring the temporal change in product enantiomeric excess after addition of the opposite enantiomer of the ligand during the reaction provides a means of probing dynamic ligand exchange in enantioselective C-H iodination catalyzed by Pd with monoprotected amino acid ligands (MPAAs). This work has general potential to provide insights about the dynamics of catalyst and ligand molecularity and exchange.

PMID:
29215885
DOI:
10.1021/jacs.7b11962

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