A Platinum(0) Complex as π-Lewis Base Catalyst for Asymmetric Friedel-Crafts Reaction

IF 2.7 3区 化学 Q2 CHEMISTRY, ORGANIC European Journal of Organic Chemistry Pub Date : 2025-02-12 DOI:10.1002/ejoc.202401458
Hao-Tian Wang, Xin-Ting Qin, Bo Jiang, Prof. Dr. Zhi-Chao Chen, Prof. Dr. Wei Du, Prof. Dr. Ying-Chun Chen
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Abstract

Here we demonstrate that a Pt0 complex can function as an efficient π-Lewis base catalyst to increase the nucleophilicity of deactivated heteroarenes upon η2-coordination and resultant π-backdonation, thus enabling asymmetric Friedel-Crafts reaction with electrophiles. A diversity of densely functionalized adducts are produced in high yields with moderate to excellent enantioselectivity. Preliminary frontier molecular orbital (FMO) calculations and in situ 1H NMR analysis support the Pt0 π-Lewis base catalytic mode.

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铂(0)配合物作非对称Friedel−Crafts反应π-Lewis碱催化剂
本文证明了Pt0配合物可以作为一个有效的π-Lewis碱催化剂,通过η - 2配位和π-反给价来提高失活杂芳烃的亲核性,从而实现与亲电试剂的不对称Friedel−Crafts反应。多种密集功能化的加合物以高收率生产,对映体选择性中等至优异。初步的前沿分子轨道(FMO)计算和原位1H NMR分析支持Pt0 π-Lewis碱催化模式。
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来源期刊
CiteScore
5.40
自引率
3.60%
发文量
752
审稿时长
1 months
期刊介绍: The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.
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