Diboron reagents have been traditionally regarded as "Lewis acids", which can react with simple Lewis base to create a significant nucleophilic character in one of boryl moieties. In particular, bis(pinacolato)diboron (B₂pin₂) reacts with simple Lewis bases, such as -heterocyclic carbenes (NHCs), phosphines and alkoxides. This review focuses on the application of trivalent nucleophilic boryl synthon in the selective preparation of organoboron compounds, mainly through metal-free catalytic diboration and the β-boration reactions of alkynes and alkenes.
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http://dx.doi.org/10.3390/molecules24010101 | DOI Listing |
J Am Chem Soc
December 2024
Department of Applied Chemistry for Environment, Graduate School of Urban Environmental Sciences, Tokyo Metropolitan University, 1-1 minami-Osawa, Hachioji 192-0397, Tokyo, Japan.
Nat Commun
November 2024
Bioland Laboratory, Guangzhou, China.
α-Functionalized Si-, Ge-, B-, Se-, and S-amide moieties are present in many medicinally active molecules, but their synthesis remains challenging. Here, we demonstrate a high-throughput synthesis using amide-sulfoxonium ylides as carbene precursors in a Si-H, Ge-H, B-H, Se-H, and S-H insertion reactions to target a wide range of α-silyl, α-geryl, α-boryl, α-selenyl, and α-sulfur (hetero)amides. The process is featured as simple operation, mild conditions, broad substrate scope, high functional group compatibility, and excellent chemoselectivity.
View Article and Find Full Text PDFInorg Chem
December 2024
State Key Laboratory of Applied Organic Chemistry (Lanzhou University), Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province, Lanzhou Magnetic Resonance Center, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
Org Lett
November 2024
Anhui Province Key Laboratory of Value-Added Catalytic Conversion and Reaction Engineering, School of Chemistry and Chemical Engineering, Hefei University of Technology, Hefei, Anhui 230009, China.
Organoboronic acids, some of the most common and widely used organoboron compounds, have not yet been used in the cobalt-catalyzed cross coupling reactions, despite cobalt demonstrating good reactivity with zinc reagents, Grignard reagents, and metal organoborates that are formed by -butyl lithium or alkaline metal alkoxide salts and organoboron esters. Herein, a highly efficient and practical cobalt-catalyzed coupling reaction of aryl/alkenyl boronic acids and alkynyl chloride under mild reaction conditions is reported. The advantages of the organoboronic acids, along with a broad functional group compatibility and the reaction's tolerance to moisture and air, enable this reaction to be a synthetically useful protocol for the construction of a C(sp)-C(sp) bond.
View Article and Find Full Text PDFJACS Au
October 2024
Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Korea.
This study aims to develop a method for the chiral analysis of organoboron compounds using nuclear magnetic resonance (NMR) spectroscopy. It addresses the longstanding challenge associated with these chiral organoboron compounds, which often require derivatization and pretreatment prior to chromatographic analysis. Our method utilizes tridentate ligands to facilitate effective ligand exchange and incorporates fluorine labels, allowing for the precise discrimination of F NMR signals.
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