A direct deoxygenative hydroborylation of ketones with hydroborane ester promoted by a combination of samarium diiodide, samarium and nickel has been developed. In this method, secondary alkyl borate esters are synthesized from unactivated ketones with hydroborane esters in one step. A broad substrate scope and excellent selectivity toward CO cleavage has been demonstrated. This approach represents a general method for the construction of versatile secondary alkyl borate esters from unactivated ketones.
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http://dx.doi.org/10.1039/d4ob01287a | DOI Listing |
Org Biomol Chem
October 2024
Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, China.
A direct deoxygenative hydroborylation of ketones with hydroborane ester promoted by a combination of samarium diiodide, samarium and nickel has been developed. In this method, secondary alkyl borate esters are synthesized from unactivated ketones with hydroborane esters in one step. A broad substrate scope and excellent selectivity toward CO cleavage has been demonstrated.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2024
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou, 730000, P. R. China.
Selective hydroboration of C-C single bonds presents a fundamental challenge in the chemical industry. Previously, only catalytic systems utilizing precious metals Ir and Rh, in conjunction with N- and P- ligands, could achieve this, ensuring bond cleavage and selectivity. In sharp contrast, we discovered an unprecedented and general transition-metal-free system for the hydroboration of C-C single bonds.
View Article and Find Full Text PDFJ Am Chem Soc
August 2022
Department of Chemistry and the Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration & Reconstruction, The Hong Kong University of Science and Technology (HKUST), Clear Water Bay, Kowloon, Hong Kong SAR 999077, China.
Although hydroboration of simple ketones and alkynes have been well-established, little is known about the unique hydroboration reactivity for ynones, a family of important building blocks. Herein we report a new reaction mode of ynones leading to structurally novel and synthetically useful but previously inaccessible products, vinyl α-hydroxylboronates, under mild ruthenium-catalyzed hydroboration conditions. This reaction features high efficiency, a broad scope, and complete chemo-, regio-, and stereoselectivity, in spite of many possible competitive pathways.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
May 2017
State Key Laboratory and Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071, China.
B(C F ) has been found to be an effective catalyst for reduction of pyridines and other electron-deficient N-heteroarenes with hydrosilanes (or hydroboranes) and amines as the reducing reagents. The success of this development hinges upon the realization of a cascade process of dearomative hydrosilylation (or hydroboration) and transfer hydrogenation. The broad functional-group tolerance (e.
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