Aldehydes and ketones influence reactivity and selectivity in nickel-catalysed Suzuki-Miyaura reactions

被引：25

作者：

Cooper, Alasdair K. ^{[1
]}

Leonard, David K. ^{[1
,3
]}

Bajo, Sonia ^{[1
,4
]}

Burton, Paul M. ^{[2
]}

Nelson, David J. ^{[1
]}

机构：

[1] Univ Strathclyde, WestCHEM Dept Pure & Appl Chem, 295 Cathedral St, Glasgow G1 1XL, Lanark, Scotland

[2] Syngenta Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England

[3] Leibniz Inst Catalysis, Albert Einstein Str 29a, D-18059 Rostock, Germany

[4] Univ Seville, CSIC, Inst Chem Res IIQ, Avda Americo Vespucio 49, Seville 41092, Spain

来源：

CHEMICAL SCIENCE | 2020年 / 11卷 / 07期

基金：

英国工程与自然科学研究理事会;

关键词：

OXIDATIVE ADDITION; RING-WALKING; ARYL HALIDES; COMPLEXES; LIGAND; NI(I); NI; TRIFLUOROMETHYLTHIOLATION; COORDINATION; PRECATALYSTS;

D O I：

10.1039/c9sc05444h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The energetically-favorable coordination of aldehydes and ketones - but not esters or amides - to Ni-0 during Suzuki-Miyaura reactions can lead either to exquisite selectivity and enhanced reactivity, or to inhibition of the reaction. Aryl halides where the C-X bond is connected to the same pi-system as an aldehyde or ketone undergo unexpectedly rapid oxidative addition to [Ni(COD)(dppf)] (1), and are selectively cross-coupled during competition reactions. When aldehydes and ketones are present in the form of exogenous additives, the cross-coupling reaction is inhibited to an extent that depends on the strength of the coordination of the pendant carbonyl group to Ni-0. This work advances our understanding of how common functional groups interact with Ni-0 catalysts and how these interactions affect workhorse catalytic reactions in academia and industry.

引用

页码：1905 / 1911

页数：7

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