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NHC-boranes have been treated as a reliable source of boryl radicals. In this study, regioselective hydroborylation of ketene dithioacetals with NHC-borane was achieved under mild conditions via a visible-light-promoted radical chain process using thiophenol as a proton donor and hydrogen atom transfer. This protocol features a low-cost catalyst, good functional group tolerance, a relatively broad range of substrate scope, and good to excellent yields. Moreover, mechanism of this hydroborylation reaction was preliminarily studied.
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http://dx.doi.org/10.1021/acs.joc.3c01642 | DOI Listing |
J Org Chem
November 2023
School of Pharmaceutical Sciences, Nanjing Tech University, Nanjing 211816, P. R. China.
NHC-boranes have been treated as a reliable source of boryl radicals. In this study, regioselective hydroborylation of ketene dithioacetals with NHC-borane was achieved under mild conditions via a visible-light-promoted radical chain process using thiophenol as a proton donor and hydrogen atom transfer. This protocol features a low-cost catalyst, good functional group tolerance, a relatively broad range of substrate scope, and good to excellent yields.
View Article and Find Full Text PDFNat Commun
May 2023
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543, Republic of Singapore.
Geminal and vicinal borosilanes are useful building blocks in synthetic chemistry and material science. Hydrosilylation/hydroborylation of unsaturated systems offer expedient access to these motifs. In contrast to the well-established transition-metal-catalyzed methods, radical approaches are rarely explored.
View Article and Find Full Text PDFChem Commun (Camb)
July 2022
School of Pharmaceutical Sciences, Nanjing Tech University, Nanjing 211816, P. R. China.
A photo-induced transition-metal-free regioselective hydroborylation of α,β-unsaturated carbonyl compounds is developed. The PhSSPh reagent was employed as the photocatalyst, and NHC-BH was used as the boron source. This transformation shows a broad substrate scope and provides a wide range of α-borylcarbonyl molecules in good to excellent yields.
View Article and Find Full Text PDFOrg Lett
February 2016
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, Karnataka, India.
A ligand controlled selective hydroborylation of alkynes to α- or β-vinylboronates has been developed using a Pd catalyst. The high α-selectivity displayed by this reaction can be switched to furnish β-vinylboronates by altering the ligand from a trialkylphosphine to N-heterocyclic carbene. A variety of terminal alkynes are shown to furnish the corresponding α- or β-vinylboronates in good to excellent selectivity and yield.
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