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Ligand-controlled NiH-catalyzed regiodivergent hydroalkylation of 2-alkenylazaarenes

Science China Chemistry 2024年第6期67卷 1935-1940页

作者： Ya-Ping Shao Zhuo-Min Chi Yong-Min Liang State Key Laboratory of Applied Organic Chemistry School of Chemistry and Chemical EngineeringLanzhou UniversityLanzhou730000China

A nickel-hydride(Ni H)-catalyzed migratory and nonmigratory hydroalkylation reaction of 2-alkenyl azaarenes with alkyl iodines has been established through strategic modulation of N-or P-donor ligands.This method enables the synthesis of diverseβ-orγ-branched aromatic N-heterocycles.The mild regiodivergent protocols exhibit wide substrate scope,excellent functional tolerance,and great reaction yield with remarkable regioselectivity.Importantly,deuterium labeling studies reveal Ni H-catalyzed interrupted chain-walking mode as the mechanism behind remotedβ-selective hydroalkylation reaction—an interesting phenomenon mediated through aromatic imine directing groups.

关键词： NiH regiodivergent hydroalkylation azaarenes interrupted chain-walking

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Ni-catalyzed regiodivergent hydrophosphorylation of enynes

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Chinese Chemical Letters 2023年第6期34卷 301-305页

作者： Sa-Na Yang Shao-Han Sun Chang-Hui Liu Xiang-Ting Min Boshun Wan Ding-Wei Ji Qing-An Chen Dalian Institute of Chemical Physics Chinese Academy of SciencesDalian 116023China University of Chinese Academy of Sciences Beijing 100049China

A regiodivergent hydrophosphorylation of enynes with phosphites has been developed using earthabundant nickel catalyst.The manipulation of regioselectivity can be achieved by regulating the insertion order of alkyne bonds with(RO)_(2)P(O)-Ni-H or R_(2)P(O)O-Ni-H species,respectively.Under the Ni/Xantphos catalysis,4,1-hydrophosphorylation is selectively obtained while the adding of acid can promote reactions towards 1,2-addition.By employing an additional Pd-H catalysis,2,1-hydrophosphorylation is also an accessible task in one-pot reaction.Mechanistic studies and analysis have also been performed to interpret the origin of the regioselective regulation.This work highlights the arts in accessing different regioisomers by diverting common elementary reaction steps.

关键词： regiodivergent Hydrophosphorylation Nickel catalysis Enynes

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Nickel-Catalyzed regiodivergent Asymmetric Cycloadditions of α,β-Unsaturated Carbonyl Compounds

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CCS Chemistry 2022年第9期4卷 3122-3133页

作者： Shi Cao Ziqi Ye Yuehua Chen Yu-Mei Lin Jiahua Fang Yuejiao Wang Boxuan Yang Lei Gong Key Laboratory of Chemical Biology of Fujian Province iChEMCollege of Chemistry and Chemical EngineeringXiamen UniversityXiamenFujian 361005

regiodivergent asymmetric cycloadditions from the same set of starting materials offer interesting opportunities for rapid construction of optically active cyclic molecules with structural diversity.However,this remains a challenging task due to the difficulty of simultaneously controlling the regio-,diastereo-,and enantioselectivity in the ring formation processes.To address this long-standing problem.

关键词： cycloaddition regiodivergent asymmetric photocatalysis visible light nickel

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Ligand controlled cobalt catalyzed regiodivergent 1,2-hydroboration of 1,3-dienes

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Science China Chemistry 2019年第3期62卷 336-340页

作者： Sihan Peng Ji Yang Guixia Liu Zheng Huang State Key Laboratory of Organometallic Chemistry Center for Excellence in Molecular Synthesis Shanghai Institute of Organic Chemistry School of Physical Science and Technology Shanghai Tech University

regiodivergent 1,2-hydroboration of 1,3-dienes with pinacolborane has been accomplished by well-defined cobalt complexes of different bidentate ligands. The iminopyridine-cobalt system is selective for Markovnikov 1,2-hydroboration to form allylboronates, while the FOXAP-cobalt(FOXAP=(S)-1-(diphenylphosphino)-2-[(S)-4-isopropyloxazolin-2-yl]ferrocene) catalyst effects the complementary anti-Markonikv 1,2-hydroboration to afford homoallyboronates with high regioselectivity.

关键词： cobalt dienes hydroboration regiodivergent

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