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

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Pd‐PEPPSI‐IHeptCl: A General‐Purpose, Highly Reactive Catalyst for the Selective Coupling of Secondary Alkyl Organozincs
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2016-08-24 , DOI: 10.1002/chem.201603603
Bruce Atwater ₁ , Nalin Chandrasoma ₁ , David Mitchell ₂ , Michael J. Rodriguez ₂ , Michael G. Organ _{1,

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Affiliation

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.

中文翻译：

Pd-PEPPSI-IHeptCl：用于仲烷基有机锌选择性偶联的通用，高反应活性催化剂

二氯[1,3-双（2,6-二-4-庚基苯基）咪唑-2-基]（3-氯吡啶基）钯（II）（Pd-PEPPSI-IHept ^Cl），一种新的，非常笨重而灵活的Pd -N-杂环卡宾（NHC）络合物已经在烷基仲锌反应物与各种氧化加成伙伴的交叉偶联中得到了高收率和出色的选择性的评估。获得了所需的直接还原消除支化产物，没有迁移迹象表明富电子和贫电子芳族化合物以及所有形式的杂芳族化合物（五元和六元）都可以迁移。令人印象深刻的是，取代基在还原消除位点（即邻位或什至二邻位）上没有任何影响，迄今为止尚未被另一种催化剂体系证明。

更新日期：2016-08-24

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