This short review summarizes our laboratory's development of benzylboronic esters as nucleophiles. Activation of the benzylboronic ester is achieved by irreversible coordination of an alkyllithium Lewis base to form a nucleophilic benzylboronate. This boronate was found to react with aldehydes, imines, ketones and alkyl bromides. A copper catalyst was employed in reactions of the boronate with epoxides and aziridines.
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http://dx.doi.org/10.1055/a-2072-2754 | DOI Listing |
Synthesis (Stuttg)
September 2023
College of Charleston, Department of Chemistry and Biochemistry, 66 George St., Charleston, SC.
This short review summarizes our laboratory's development of benzylboronic esters as nucleophiles. Activation of the benzylboronic ester is achieved by irreversible coordination of an alkyllithium Lewis base to form a nucleophilic benzylboronate. This boronate was found to react with aldehydes, imines, ketones and alkyl bromides.
View Article and Find Full Text PDFChem Sci
January 2018
Department of Chemistry , University of Wisconsin-Madison , 1101 University Avenue, Madison , Wisconsin 53706 , USA . Email:
The generation and intermolecular functionalisation of carbon-centred radicals has broad potential synthetic utility. Herein, we show that benzylic radicals may be generated electrochemically from benzylboronate derivatives at low electrode potentials ( -0.3 V CpFe) single electron oxidation.
View Article and Find Full Text PDFJ Am Chem Soc
June 2013
Department of Chemistry, University of California, Berkeley , California 94270, United States.
Most functionalizations of C-H bonds by main-group reagents occur at aryl or methyl groups. We describe a highly regioselective borylation of secondary benzylic C-H bonds catalyzed by an iridium precursor and 3,4,7,8-tetramethyl-1,10-phenanthroline as the ligand. The reaction is directed to the benzylic position by a hydrosilyl substituent.
View Article and Find Full Text PDFOrg Lett
July 2011
Waseda Institute for Advanced Study, Shinjuku, Tokyo, 169-8050, Japan.
The chemoselective Pd-catalyzed Suzuki-Miyaura cross-coupling reaction using a diborylmethane is reported. The use of an equimolar amount of base with a diborylmethane realized chemoselective coupling for the synthesis of various benzylboronate derivatives. Sterically hindered aryl bromides can give products in moderate to excellent yields.
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