Pd(II)-Catalyzed Direct Sulfonylation of Benzylamines Using Sodium Sulfinates

被引：26

作者：

Karmakar, Ujjwal ^{[1
]}

Samanta, Rajarshi ^{[1
]}

机构：

[1] Indian Inst Technol Kharagpur, Dept Chem, Kharagpur 721302, W Bengal, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 05期

关键词：

H BOND FUNCTIONALIZATION; QUINOLINE N-OXIDES; HIGHLY EFFICIENT SYNTHESIS; C-S; CATALYZED DIRECT; C(SP(2))-H BONDS; ORTHO-C(SP(2))-H BONDS; REDUCTIVE AMINATION; VINYL SULFONES; PALLADIUM;

D O I：

10.1021/acs.joc.8b03098

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Pd(II)-catalyzed direct sulfonylation of benzylamines with sodium sulfinates using a removable bidentate directing group is illustrated. The transformation is highly regioselective and tolerates wide functional groups. The mechanistic study reveals that radical species are involved in this reaction. This method delivers a direct synthetic strategy to obtain highly functionalized sulfonylated benzylamines.

引用

页码：2850 / 2861

页数：12

共 95 条

[1] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].

Ackermann, Lutz .

CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345

[2]

Acton Q., 2013, ADV INTRACELLULAR SP, V1st, P10

[3]

Aneja B, 2016, ORG BIOMOL CHEM, V14, P10599, DOI [10.1039/C6OB01718E, 10.1039/c6ob01718e]

[4] Structure-activity relationships (SAR) and structure-kinetic relationships (SKR) of sulphone-based CRTh2 antagonists [J].

Antonia Buil, Maria ;

Calbet, Marta ;

Castillo, Marcos ;

Castro, Jordi ;

Esteve, Cristina ;

Ferrer, Manel ;

Forns, Pilar ;

Gonzalez, Jacob ;

Lopez, Sara ;

Roberts, Richard S. ;

Sevilla, Sara ;

Vidal, Bernat ;

Vidal, Laura ;

Vilaseca, Pere .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 113 :102-133

[5] Second-Generation Process Research Towards Eletriptan: A Fischer Indole Approach [J].

Ashcroft, Christopher P. ;

Hellier, Paul ;

Pettman, Alan ;

Watkinson, Simon .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2011, 15 (01) :98-103

[6] Synthesis of Primary Amines by One-Pot Reductive Amination of Aldehydes [J].

Ayedi, Mohamed Ali ;

Le Bigot, Yves ;

Ammar, Houcine ;

Abid, Souhir ;

El Gharbi, Rachid ;

Delmas, Michel .

SYNTHETIC COMMUNICATIONS, 2013, 43 (16) :2127-2133

[7] Ru/Cu Photoredox or Cu/Ag Catalyzed C4-H Sulfonylation of 1-Naphthylamides at Room Temperature [J].

Bai, Peirong ;

Sun, Suyan ;

Li, Zexian ;

Qiao, Huijie ;

Su, Xiaoxue ;

Yang, Fan ;

Wu, Yusheng ;

Wu, Yangjie .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (23) :12119-12127

[8] Copper-Catalyzed Direct, Regioselective Arylamination of N-Oxides: Studies To Access Conjugated π-Systems [J].

Biswas, Aniruddha ;

Karmakar, Ujjwal ;

Nandi, Shiny ;

Samanta, Rajarshi .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (17) :8933-8942

[9] Copper-Catalyzed Regioselective Cascade Alkylation and Cyclocondensation of Quinoline N-Oxides with Diazo Esters: Direct Access to Conjugated π-Systems [J].

Biswas, Aniruddha ;

Karmakar, Ujjwal ;

Pal, Arun ;

Samanta, Rajarshi .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (39) :13826-13830

[10] Indirect ortho functionalization of substituted toluenes through ortho olefination of N,N-dimethylbenzylamines tuned by the acidity of reaction conditions [J].

Cai, Guixin ;

Fu, Ye ;

Li, Yizhou ;

Wan, Xiaobing ;

Shi, Zhangjie .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (24) :7666-7673

← 1 2 3 4 5 6 7 8 9 10 →