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含硅烷基-NHC螯合配体的铁催化剂：烯烃硼氢化与脱氢硼化的控制因素

Iron Catalysts with Silyl-NHC Chelate Ligands: Controlling Factors for Hydroboration vs. Dehydrogenative Borylation of Olefins.

作者信息

Ishiwata Nozomu, Komuro Takashi, Takahashi Kasumi, Zenzai Yasuaki, Tobita Hiromi, Hashimoto Hisako

机构信息

Department of Chemistry, Graduate School of Science, Tohoku University, 6-3 Aramaki Aza-Aoba, Aoba-ku, Sendai, 980-8578, Japan.

出版信息

Chem Asian J. 2025 Aug;20(15):e00709. doi: 10.1002/asia.202500709. Epub 2025 Jul 21.

DOI:10.1002/asia.202500709
PMID:40689858
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12392704/
Abstract

Various iron complexes 1, featuring silyl-NHC chelate ligands (NHC = N-heterocyclic carbene) were synthesized and investigated for their catalytic performance in the borylation reactions of olefins. Complexes 1 facilitated both hydroboration and dehydrogenative borylation of olefins with HBpin, yielding borylalkanes and borylalkenes, respectively. The selectivity between the two pathways was found to be governed by the steric effect of a substituent on one nitrogen atom of the NHC moiety. Possible catalytic mechanisms including hydroborato and β-agostic-alkyl complexes as potential resting states or intermediates are proposed based on stoichiometric reactions.

摘要

合成了各种具有甲硅烷基-NHC螯合配体（NHC = N-杂环卡宾）的铁配合物1，并研究了它们在烯烃硼氢化反应中的催化性能。配合物1促进了烯烃与HBpin的硼氢化反应和脱氢硼氢化反应，分别生成硼烷基烷烃和硼烷基烯烃。发现这两种途径之间的选择性受NHC部分一个氮原子上取代基的空间效应控制。基于化学计量反应，提出了包括硼氢化物和β-配位-烷基配合物作为潜在静止态或中间体的可能催化机理。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fed6/12392704/16856ea8ad1c/ASIA-20-e00709-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fed6/12392704/8a043b63b50f/ASIA-20-e00709-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fed6/12392704/b6966f44a277/ASIA-20-e00709-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fed6/12392704/2490dfdfb975/ASIA-20-e00709-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fed6/12392704/30dacbc1e91d/ASIA-20-e00709-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fed6/12392704/16856ea8ad1c/ASIA-20-e00709-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fed6/12392704/8a043b63b50f/ASIA-20-e00709-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fed6/12392704/b6966f44a277/ASIA-20-e00709-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fed6/12392704/2490dfdfb975/ASIA-20-e00709-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fed6/12392704/30dacbc1e91d/ASIA-20-e00709-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fed6/12392704/16856ea8ad1c/ASIA-20-e00709-g002.jpg

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本文引用的文献

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X-type silyl ligands for transition-metal catalysis.用于过渡金属催化的X型硅基配体。
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Iron complexes supported by silyl-NHC chelate ligands: synthesis and use for double hydroboration of nitriles.硅烷基-NHC螯合配体支持的铁配合物：腈的双硼氢化反应的合成与应用
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Iron-Catalyzed Reductive Cross-Coupling of Alkyl Electrophiles with Olefins.铁催化的烷基亲电试剂与烯烃的还原交叉偶联反应
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Cobalt-N-Heterocyclic Carbene Complexes in Catalysis.催化中的钴-N-杂环卡宾配合物
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