A Ni-Ir Dual Photocatalytic Liebeskind Coupling of Sulfonium Salts for the Synthesis of 2-Benzylpyrrolidines

被引：26

作者：

Varga, Balint ^{[1
]}

Gonda, Zsombor ^{[1
]}

Toth, Balazs L. ^{[1
]}

Kotschy, Andras ^{[2
]}

Novak, Zoltan ^{[1
]}

机构：

[1] Eotvos Lorand Univ, Inst Chem, ELTE Lendulet Catalysis & Organ Synth Res Grp, Pazmany Peter Stny 1-A, H-1117 Budapest, Hungary

[2] Servier Res Inst Med Chem, Zahony Utca 7, H-1031 Budapest, Hungary

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 10期

关键词：

Sulfonium salts; Cross-coupling; Iridium; Nickel; Photoredox catalysis; CARBOXYLIC-ACIDS; DECARBOXYLATIVE ALKYLATION; CATALYZED CARBOAMINATION; PHOTOREDOX CATALYSIS; MERGING PHOTOREDOX; LIGHT; NICKEL; ALKYLSILICATES; ACCELERATION; CHEMISTRY;

D O I：

10.1002/ejoc.201900957

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method has been developed for the synthesis of 2-benzylpyrrolidines utilizing cross-coupling and photoredox catalysis. Using a well-established dual Ni-Ir system, we were able to successfully couple benzylsulfonium salts with proline utilizing radical forming through CO2 extrusion. This enabled the simple one-step synthesis of 2-benzylpyrrolidines from stable, inexpensive starting materials.

引用

收藏

页码：1466 / 1471

页数：6

相关论文

共 62 条

[1] POSITIVELY CHARGED LIGANDS - THE SYNTHESIS, STRUCTURE, AND BONDING OF SULFONIUM ION COMPLEXES OF TRANSITION-METALS AND EVIDENCE FOR A METAL-INDUCED ACCELERATION OF THEIR DEALKYLATION [J].

ADAMS, RD ;

BLANKENSHIP, C ;

SEGMULLER, BE ;

SHIRALIAN, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (13) :4319-4326

[2] Mild Conditions for Pd-Catalyzed Carboamination of N-Protected Hex-4-enylamines and 1-, 3-, and 4-Substituted Pent-4-enylamines. Scope, Limitations, and Mechanism of Pyrrolidine Formation [J].

Bertrand, Myra Beaudoin ;

Neukom, Joshua D. ;

Wolfe, John P. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22) :8851-8860

[3]

Bloom S, 2018, NAT CHEM, V10, P205, DOI [10.1038/NCHEM.2888, 10.1038/nchem.2888]

[4] Visible light-driven organic photochemical synthesis in China [J].

Chen, Yiyun ;

Lu, Liang-Qiu ;

Yu, Da-Gang ;

Zhu, Cheng-Jian ;

Xiao, Wen-Jing .

SCIENCE CHINA-CHEMISTRY, 2019, 62 (01) :24-57

[5] Photoredox-Catalysed Decarboxylative Alkylation of N-Heteroarenes with N-(Acyloxy)phthalimides [J].

Cheng, Wan-Min ;

Shang, Rui ;

Fu, Ming-Chen ;

Fu, Yao .

CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (11) :2537-2541

[6]

Couture A., 1998, J CHEM SOC P1, V8, P1403

[7] Visible-Light Photocatalytic Reduction of Sulfonium Salts as a Source of Aryl Radicals [J].

Donck, Simon ;

Baroudi, Abdulkader ;

Fensterbank, Louis ;

Goddard, Jean-Philippe ;

Ollivier, Cyril .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (08) :1477-1482

[8] Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Alkyl Bromides: Et3N as the Terminal Reductant [J].

Duan, Zhengli ;

Li, Wu ;

Lei, Aiwen .

ORGANIC LETTERS, 2016, 18 (16) :4012-4015

[9] Photocatalysis for the formation of the C-C bond [J].

Fagnoni, Maurizio ;

Dondi, Daniele ;

Ravelli, Davide ;

Albini, Angelo .

CHEMICAL REVIEWS, 2007, 107 (06) :2725-2756

[10] N,N-6-BIS-[2-(3,4-DIHYDROXYBENZYL)PYRROLIDINYL]HEXANE, A POTENT, SELECTIVE, ORALLY-ACTIVE DOPAMINE ANALOG WITH HYPOTENSIVE AND DIURETIC ACTIVITY [J].

FISHER, LE ;

ROSENKRANZ, RP ;

CLARK, RD ;

MUCHOWSKI, JM ;

MCCLELLAND, DL ;

MICHEL, A ;

CAROON, JM ;

GALEAZZI, E ;

EGLEN, R ;

WHITING, RL .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (20) :2371-2376

← 1 2 3 4 5 6 7 →