An expedient synthesis of α-aminoboronic acid derivatives via cobalt-catalyzed remote site-selective hydroboration of unactivated alkenes is described herein. The strategy is characterized by its simplicity, site-selectivity, and wide substrate scope, as both terminal and internal alkenes could undergo the reaction smoothly, affording the corresponding products in good yields. According to the mechanism, Co-H is generated from Co(acac) in the presence of HBpin, which starts the chain-walking strategy via a series of alkene insertion and β-H elimination process.
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Cobalt-Catalyzed Remote Site-Selective Hydroboration of Unactivated Alkenes via Chain-Walking Strategy.
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Institute of Next Generation Matter Transformation, College of Material Sciences Engineering, Huaqiao University, Xiamen, Fujian 361021, China.
An expedient synthesis of α-aminoboronic acid derivatives via cobalt-catalyzed remote site-selective hydroboration of unactivated alkenes is described herein. The strategy is characterized by its simplicity, site-selectivity, and wide substrate scope, as both terminal and internal alkenes could undergo the reaction smoothly, affording the corresponding products in good yields. According to the mechanism, Co-H is generated from Co(acac) in the presence of HBpin, which starts the chain-walking strategy via a series of alkene insertion and β-H elimination process.
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College of Pharmacy, Guizhou Engineering Laboratory for Synthetic Drugs, Guizhou University, Guiyang, Guizhou 550025, People's Republic of China.
Heteroatomic groups in alkenes typically direct thermodynamically favored chain walking of C═C bonds toward themselves, thereby facilitating C-H bond functionalization near the heteroatoms. We present herein an efficient cobalt-catalyzed contra-thermodynamic remote hydroboration of alkenylboronates with pinacolborane to synthesize chiral 1,-diboronates. This protocol features a broad substrate scope, high functional group tolerance, and excellent enantioselectivity.
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Angew Chem Int Ed Engl
August 2023
State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan, 410082, P. R. China.
Enantioselective functionalization of racemic alkyl halides is an efficient strategy to assemble complex chiral molecules, but remains one of the biggest challenges in organic chemistry. The distant and selective activation of unreactive C-H bonds in alkyl halides has received growing interest as it enables rapid generation of molecular complexity from simple building blocks. Here, we reported a cobalt-catalyzed remote borylation of alkyl (pseudo)halides (alkyl-X, X=I, Br, Cl, OTs) with pinacolborane (HBpin) and presented a robust approach for the generation of valuable chiral secondary organoboronates from racemic alkyl halides.
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