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Gearing between the a-carbon atom and the nitrogen atom of an amino acid
ligand relays chiral information to the Pd(II) center, which is then capable of performing asymmetric C−H cleavage. In this communication, we report on the first example of
Pd(II)-catalyzed enantioselective alkylation of sp2 and
sp3 C−H bonds with boronic acids.
• For the original publication, please see Angew. Chem. Int. Ed., 2008, 47,
4761. [Link]
O-Methyl hydroxamic acids, as carboxylic acid derivatives,
undergo b-C−H insertion by Pd(II)
catalysts. The resulting intermediates can subsequent be coupled with boronic acids to form new carbon−carbon
bonds. Air, the most environmentally benign and inexpensive oxidant available, is used to regenerate the catalytically active Pd(II) species following reductive elimination.
• For the original publication, please see J. Am. Chem. Soc., 2008, 130, 7190. [Link]
Characterization of a trinuclear C−H activation intermediate (shown below) provides
insights into the origin of the reactivity and stereoselectivity of Pd(II)
insertion into neighboring inert C−H bonds.
• For the original publication, please see Angew. Chem. Int. Ed. 2005, 44, 2122. [Link]
Thank you for your interest in the Yu Group! This website provides up-to-date information concerning our research in the area of transition metal-catalyzed C−H activation. For prospective graduate students and
postdoctoral fellows, relevant research projects that are currently in progress in our
laboratory are summarized in the Research and Publications sections. A downloadable PDF file of our published work is also included. The Members section
should provide a perspective on the composition of our group, both in terms of size and diversity.
Prof. Jin-Quan
Yu
yu200@scripps.edu
