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α-卤代氮杂环对（双二苯基膦）镍催化的铃木-宫浦交叉偶联反应的抑制作用。

Inhibition of (dppf)nickel-catalysed Suzuki-Miyaura cross-coupling reactions by α-halo-N-heterocycles.

作者信息

Cooper Alasdair K, Greaves Megan E, Donohoe William, Burton Paul M, Ronson Thomas O, Kennedy Alan R, Nelson David J

机构信息

WestCHEM Department of Pure and Applied Chemistry, University of Strathclyde 295 Cathedral Street Glasgow G1 1XL Scotland UK

Chemical Development, Pharmaceutical Technology and Development, Operations, AstraZeneca Macclesfield SK10 2NA UK.

出版信息

Chem Sci. 2021 Oct 11;12(42):14074-14082. doi: 10.1039/d1sc04582b. eCollection 2021 Nov 3.

DOI:10.1039/d1sc04582b
PMID:34760191
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8565371/
Abstract

A nickel/dppf catalyst system was found to successfully achieve the Suzuki-Miyaura cross-coupling reactions of 3- and 4-chloropyridine and of 6-chloroquinoline but not of 2-chloropyridine or of other α-halo-N-heterocycles. Further investigations revealed that chloropyridines undergo rapid oxidative addition to [Ni(COD)(dppf)] but that α-halo-N-heterocycles lead to the formation of stable dimeric nickel species that are catalytically inactive in Suzuki-Miyaura cross-coupling reactions. However, the corresponding Kumada-Tamao-Corriu reactions all proceed readily, which is attributed to more rapid transmetalation of Grignard reagents.

摘要

发现镍/双(二苯基膦基)甲烷催化剂体系能够成功实现3-氯吡啶和4-氯吡啶以及6-氯喹啉的铃木-宫浦交叉偶联反应，但不能实现2-氯吡啶或其他α-卤代氮杂环化合物的该反应。进一步研究表明，氯吡啶能迅速与[Ni(COD)(dppf)]发生氧化加成反应，但α-卤代氮杂环化合物会导致形成稳定的二聚镍物种，这些物种在铃木-宫浦交叉偶联反应中无催化活性。然而，相应的熊田-玉尾-古川反应都能顺利进行，这归因于格氏试剂的转金属化反应更快。

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