The regioselective hydroboration of aliphatic internal alkenes remains a great challenge. Reported herein is an iridium-catalyzed hydroboration of aliphatic internal alkenes, providing distal-borylated products in good to excellent yields with high regioselectivity (up to 99:1). We also demonstrate that the C-B bond of the distal-borylated product can be readily converted into other functional groups. DFT calculations indicate that the reaction proceeds through an unexpected Ir /Ir cycle.
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http://dx.doi.org/10.1002/anie.201902464 | DOI Listing |
Inorg Chem
September 2024
School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. China.
Chemical recycling is a promising strategy to establish a circular plastic economy, and it is still in an early stage of development. In this work, the reductive depolymerization of polyesters and polycarbonates into their corresponding borylated alcohols promoted by heterogeneous lanthanum materials was described. Grafting the easily accessible lanthanum tris(aminobenzyl) complex La(CHCHNMe-) () onto the partially dehydroxylated silica support SBA-15 (SBA-15 or SBA-15) gave the inorganic-organic hybrid materials @SBA-15 and @SBA-15.
View Article and Find Full Text PDFACS Catal
August 2024
Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9/163-AC, Wien A-1060, Austria.
A stereo- and regioselective Mn(I)-catalyzed hydroboration of terminal alkynes with pinacolborane (HBPin) is described. The hydroboration reaction is highly -selective in the case of aryl alkynes and -selective in the case of aliphatic alkynes. The reaction requires no additives or solvents and proceeds with a catalyst loading of 1 mol % at 50-70 °C.
View Article and Find Full Text PDFOrg Biomol Chem
July 2024
Department of Chemistry and Material Science, College of Science, Nanjing Forestry University, Nanjing 210037, China.
The hydroboration and hydrosilylation of alkenes catalyzed by the unsymmetrical β-diketiminate magnesium methyl complex [(Nacnac)MgMe (THF)] (1) have been reported. When complex 1 was employed as a highly efficient catalyst in the hydroboration of various alkenes with HBpin, only the -Markovnikov hydroboration products were obtained in high yields and with high regioselectivities under mild reaction conditions (60 °C). To our surprise, it showed different regioselectivities in the hydrosilylation of a range of alkenes with PhSiH.
View Article and Find Full Text PDFJ Org Chem
June 2024
Main Group Organometallics Optoelectronic Materials and Catalysis Lab, Department of Chemistry, National Institute of Technology, Calicut 673601, India.
Herein, we designed and synthesized a series of air-stable, cost-effective, and readily synthesizable iron(III) salen complexes ( and ) for facilitating the selective hydroboration of ketones and unactivated imines with pinacolborane in the absence of any additive. These catalyst systems exhibited good yields, chemoselectivity, high atom economy, and a broad substrate scope under mild reaction conditions with a minimal catalyst loading of 0.2 mol %.
View Article and Find Full Text PDFAdv Sci (Weinh)
July 2024
Institute of Organic Chemistry, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Organoboron compounds have a wide range of applications in numerous research fields, and methods to incorporate them in biomolecules are much sought after. Here, on-resin chemical syntheses of aliphatic and vinylogous peptide boronic acids are presented by transition metal-catalyzed late-stage hydroboration of alkene and alkyne groups in peptides and peptoids, for example on allyl- and propargylglycine residues, using readily available chemicals. These methods yield peptide boronic acids with much shorter linkers than previously reported on-resin methods.
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