II-II Stacking Complex Induces Three-Component Coupling Reactions To Synthesize Functionalized Amines

被引：24

作者：

Zhang, Tong ^{[1
]}

Vanderghinste, Jaro ^{[1
]}

Guidetti, Andrea ^{[2
]}

Van Doorslaer, Sabine ^{[2
]}

Barcaro, Giovanni ^{[3
]}

Monti, Susanna ^{[4
]}

Das, Shoubhik ^{[1
]}

机构：

[1] Univ Antwerp, Dept Chem, Groenenborgerlaan 171, B-2020 Antwerp, Belgium

[2] Univ Antwerp, BIMEF, Univ Pl 1, B-2610 Antwerp, Belgium

[3] CNR IPCF, Inst Chem & Phys Proc, I-56126 Pisa, Italy

[4] CNR ICCOM, Inst Chem Organometall Cpds, I-56126 Pisa, Italy

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2022年 / 61卷 / 49期

关键词：

Ionic Complexes; Noncovalent Interactions; Visible Light; alpha-Amino Radicals; LIGHT PHOTOREDOX CATALYSIS; DONOR-ACCEPTOR COMPLEX; C-H BONDS; NONCOVALENT PI INTERACTIONS; ALPHA-AMINOALKYL RADICALS; ENANTIOSELECTIVE ADDITION; ASYMMETRIC CATALYSIS; CONJUGATE ADDITIONS; SITE-SELECTIVITY; HANTZSCH ESTER;

D O I：

10.1002/anie.202212083

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

pi-pi stacking and ion-pairing interactions induced the generation of a-amino radicals under the irradiation of visible light without the requirement of an expensive photocatalyst. This strategy enabled the construction of functionalized amines via three-component coupling reactions with broad scope (we report > 50 examples with an up to 90 % yield). This synthetic pathway also delivered complex functionalized amines with a very high yield. Quantum chemistry Density Functional Theory (DFT) calculations identified pi-pi stacked ionic complexes; time-dependent DFT was employed to simulate the absorption spectra, and nudged elastic band (NEB) methodology provided a possible interaction/reaction picture of the selected species.

引用

页数：8

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