Copper-catalyzed reductive coupling of aryl sulfonyl chlorides with H-phosphonates leading to S-aryl phosphorothioates

被引：99

作者：

Bai, Jie ^{[1
]}

Cui, Xiuling ^{[1
,2
,3
]}

Wang, Hui ^{[1
]}

Wu, Yangjie ^{[1
]}

机构：

[1] Zhengzhou Univ, Dept Chem, Henan Key Lab Chem Biol & Organ Chem, Key Lab Appl Chem Henan Univ, Zhengzhou 450052, Peoples R China

[2] Huaqiao Univ, Xiamen Key Lab Ocean & Gene Drugs, Sch Biomed Sci, Xiamen 361021, Peoples R China

[3] Huaqiao Univ, Inst Mol Med, Engn Res Ctr Mol Med, Chinese Educ Minist, Xiamen 361021, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 64期

关键词：

RAPID INJECTION NMR; C-H; MILD CONDITIONS; GENERAL-METHOD; ESTERS; INTERMEDIATE; FUNCTIONALIZATION; INVOLVEMENT; DERIVATIVES; FORMAMIDES;

D O I：

10.1039/c4cc02693d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient protocol for copper-catalyzed reductive cross-coupling of aryl sulfonyl chlorides with H-phosphonates has been developed. The various S-aryl phosphorothioates were afforded in up to 86% yield for 20 examples. This protocol features high efficiency, wide functional group tolerance, commercially available aryl sulfonyl chlorides as starting materials and base-free conditions.

引用

收藏

页码：8860 / 8863

页数：4

相关论文

共 48 条

[1] Copper(II)/H2O2-mediated DNA cleavage:: Involvement of a copper(III) species in H-atom abstraction of deoxyribose units [J].

Amine, A ;

Atmani, Z ;

El Hallaoui, A ;

Giorgi, M ;

Pierrot, M ;

Réglier, M .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (01) :57-60

[2] Organocuprate cross-coupling: The central role of the copper(III) intermediate and the importance of the Copper(I) precursor [J].

Bertz, Steven H. ;

Cope, Stephen ;

Dorton, Donna ;

Murphy, Michael ;

Ogle, Craig A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (37) :7082-7085

[3] Rapid injection NMR in mechanistic organocopper chemistry. Preparation of the elusive copper(III) intermediate [J].

Bertz, Steven H. ;

Cope, Stephen ;

Murphy, Michael ;

Ogle, Craig A. ;

Taylor, Brad J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (23) :7208-+

[4] Rapid Injection NMR Reveals η3 'π-Allyl' CuIII Intermediates in Addition Reactions of Organocuprate Reagents [J].

Bertz, Steven H. ;

Hardin, Richard A. ;

Murphy, Michael D. ;

Ogle, Craig A. ;

Richter, Joshua D. ;

Thomas, Andy A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (23) :9557-9560

[5] Copper-Catalyzed Synthesis of Azaspirocyclohexadienones from α-Azido-N-arylamides under an Oxygen Atmosphere [J].

Chiba, Shunsuke ;

Zhang, Line ;

Lee, Jian-Yuan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (21) :7266-+

[6] Progress in antisense oligonucleotide therapeutic [J].

Crooke, ST ;

Bennett, CF .

ANNUAL REVIEW OF PHARMACOLOGY AND TOXICOLOGY, 1996, 36 :107-129

[7] An efficient synthesis of cyclic IDP- and cyclic 8-bromo-IDP-carbocyclic-riboses using a modified hata condensation method to form an intramolecular pyrophosphate linkage as a key step. An entry to a general method for the chemical synthesis of cyclic ADP-ribose analogues [J].

Fukuoka, M ;

Shuto, S ;

Minakawa, N ;

Ueno, Y ;

Matsuda, A .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (17) :5238-5248

[8] NMR-detection of Cu(III) intermediates in substitution reactions of alkyl halides with Gilman cuprates [J].

Gaertner, Tobias ;

Henze, Wolfram ;

Gschwind, Ruth M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (37) :11362-+

[9] Novel and General Method for the Formation of S-Aryl, Se-Aryl, and Te-Aryl Phosphorochalcogenoates [J].

Gao, Yu-Xing ;

Tang, Guo ;

Cao, Yu ;

Zhao, Yu-Fen .

SYNTHESIS-STUTTGART, 2009, (07) :1081-1086

[10]

Gou C., 2010, ANGEW CHEM INT EDIT, V49, P5558

← 1 2 3 4 5 →