Pd-PEPPSI-IHeptCl: A General-Purpose, Highly Reactive Catalyst for the Selective Coupling of Secondary Alkyl Organozincs

被引：46

作者：

Atwater, Bruce ^{[1
]}

Chandrasoma, Nalin ^{[1
]}

Mitchell, David ^{[4
]}

Rodriguez, Michael J. ^{[4
]}

Organ, Michael G. ^{[1
,2
,3
]}

机构：

[1] York Univ, Dept Chem, 4700 Keele St, Toronto, ON M3J 1P3, Canada

[2] Univ Ottawa, CCRI, Ottawa, ON, Canada

[3] Univ Ottawa, Dept Chem, Ottawa, ON, Canada

[4] Lilly Res Labs, Indianapolis, IN 46285 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 41期

基金：

加拿大自然科学与工程研究理事会;

关键词：

cross-coupling; palladium; PEPPSI; secondary alkylzinc; synthetic methods; CROSS-COUPLINGS; ARYL CHLORIDES; REAGENTS; BROMIDES; HALIDES; NUCLEOPHILES;

D O I：

10.1002/chem.201603603

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Dichloro[1,3-bis(2,6-di-4-heptylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) (Pd-PEPPSI-IHept(Cl)), a new, very bulky yet flexible Pd-N-heterocyclic carbene (NHC) complex has been evaluated in the cross-coupling of secondary alkylzinc reactants with a wide variety of oxidative addition partners in high yields and excellent selectivity. The desired, direct reductive elimination branched products were obtained with no sign of migratory insertion across electron-rich and electron-poor aromatics and all forms of heteroaromatics (five and six membered). Impressively, there is no impact of substituents at the site of reductive elimination (i.e., ortho or even di-ortho), which has not yet been demonstrated by another catalyst system to date.

引用

页码：14531 / 14534

页数：4

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