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Metal-free directed C-H borylation of 2-(N-methylanilino)-5-fluoropyridines and 2-benzyl-5-fluoropyridines

chinese chemical Letters 2022年第4期33卷 2005-2008页

作者： Gaorong Wu Xiaobo Xu Shuai Wang Lu chen Binghan Pang Tao Ma Yafei Ji Engineering Research center of Pharmaceutical Process chemistry Ministry of EducationSchool of PharmacyEast China University of Science and TechnologyShanghai 200237China School of chinese Materia Medica Beijing University of Chinese MedicineLiangxiang CampusBeijing 102488China

A novel method for metal-free C-H borylation of 2-(N-methylanilino)-5-fluoropyridines and 2-benzyl-5-fluoropyridines has been reported. The 5-fluoropyridine directed borylation reaction exhibited high efficiency and site exclusivity. The useful protocol could be executed on a gram-scale easily and the borylated products showed good derivatization applications. Moreover, the practicality of the strategy was expanded by the fact that the directing group could be removed in an acceptable yield.

关键词： Metal-free C-H borylation 2-(N-Methylanilino)-5-fluoropyridines 2-Benzyl-5-fluoropyridines BBr3

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Iron-catalysed c(sp^(2))-h borylation with Expanded Functional Group Tolerance

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chinese Journal of chemistry 2022年第24期40卷 2875-2881页

作者： Luke Britton Jamie h.Docherty Gary S.Nichol Andrew P.Dominey Stephen P.Thomas EaStchEM School of chemistry University of EdinburghEdinburghEH93FJ United Kingdom GSK Medicines Research centre StevenageSG12NY United Kingdom

Arene c(sp^(2))-h bond borylation offers direct and efficient access to aryl boronic esters.Using in situ catalyst activation and photoirradiation,the iron-catalysed c(sp^(2))-h borylation reaction of carboarenes,pyrroles,and indoles has been developed using only bench-stable pre-catalysts and reagents.Good functional group tolerance was observed including those not reported using previous methods(ArNh_(2),ArOh,ArSiR_(3),ArP(O)(O)_(2),Arc(O)NR_(2)).Mechanistic studies revealed iron-catalysed reductive deoxygenation,c—F protodefluorination,and a demethylation of aryl methyl ethers by c—O sigma bond hydroboration.

关键词： Iron Earth-abundant C-H borylation Boron Photochemistry

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Protecting-group-free ortho-c–h borylation of anilines enabled by mesoionic carbene-Ir complex

Green Synthesis and Catalysis

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Green Synthesis and catalysis 2023年第4期4卷 300-305页

作者： Zengyu Zhang Shiqing huang Wei Liu Liang-Liang Zhao chubin hu Xiaoyu Yan Key Laboratory of Advanced Light conversion Materials and Biophotonics Department of ChemistryRenmin University of ChinaBeijing 100872China

We describe an iridium-catalyzed ortho-selective c–h borylation of unprotected anilines.The employing strongσ-donating cyclometalated mesoionic carbene as c^c bidentate ligand is crucial for the high ortho-selectivity.computational studies support outer-sphere X–h⋅⋅⋅O_(boryl) hydrogen bond interactions,which are strengthened by bidentate c^c ligand introduction.The method shows broad substrate scope and high functional group tolerance.

关键词： Protecting-group-free C-H borylation hydrogen bonding Regioselectivity Mesoionic carbene

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Transition Metal catalyzed Direct Oxidative borylation of c--h Bonds

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chinese Journal of chemistry 2018年第10期36卷 950-954页

作者： Zhong-Tao Jiang Bi-qin Wang Zhang-Jie Shi college of chemistry and Materials Science Sichuan Normal University Chengdu Sichuan 610068 China Department of chemistry Fudan University Shanghai 200433 China

Organoboron is well-developed and broadly utilized organometallic reagents in organic synthesis due to its extraordinary performances in transition-metal catalyzed c-c and c-X bonds construction. catalytic c--h borylation and further transformations catalyzed by transition metal catalysts in the absence of oxidants were well studied in decades. however, as known, transition metal catalyzed oxidative C-H borylations were not reviewed up to date. In this article the oxidative borylation of c（sp2）-h and c（sp3）-h bonds were summarized and their mechanisms were also accounted.

关键词： C-H borylation oxidation organoboron transition metal catalysis

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