Acid-catalyzed oxidative cleavage of S-S and Se-Se bonds with DEAD: efficient access to sulfides and selenides

被引：37

作者：

An, Rui ^{[1
,2
,3
]}

Liao, Lihao ^{[1
,2
]}

Liu, Xiang ^{[1
,2
]}

Song, Shuqin ^{[3
]}

Zhao, Xiaodan ^{[1
,2
]}

机构：

[1] Sun Yat Sen Univ, Sch Chem, Inst Organ Chem, Guangzhou 510275, Guangdong, Peoples R China

[2] Sun Yat Sen Univ, Sch Chem, MOE Key Lab Bioinorgan & Synthet Chem, Guangzhou 510275, Guangdong, Peoples R China

[3] Sun Yat Sen Univ, Sch Mat Sci & Engn, Guangzhou 510275, Guangdong, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2018年 / 5卷 / 24期

基金：

中国国家自然科学基金;

关键词：

METAL-FREE SULFENYLATION; REGIOSELECTIVE SULFENYLATION; DIETHYL AZODICARBOXYLATE; UNSYMMETRICAL DIARYL; GREENER CONDITIONS; MITSUNOBU REACTION; ARYLBORONIC ACIDS; AMINO-ACIDS; SULFUR; DEHYDROGENATION;

D O I：

10.1039/c8qo00909k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An acid/DEAD system for efficient oxidative cleavage of S-S and Se-Se bonds to generate chalcogenium ions has been developed. These ions could be captured by nucleophile-tethered alkenes and nucleophilic aryl reagents such as arylboronic acids and arenes to afford diverse chalcogenides. Mechanistic studies revealed that an N-sulfenylhydrazine intermediate was involved in the transformations.

引用

页码：3557 / 3561

页数：5

共 74 条

[1] SELECTIVE OXIDATION OF SULFUR-CONTAINING AMINO ACIDS BY DIETHYL AZODICARBOXYLATE [J].

AXEN, R ;

CHAYKOVSKY, M ;

WITKOP, B .

JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (12) :4117-+

[2] Efficient dehydrogenation of 1,2,3,4-tetrahydroquinolines mediated by dialkyl azodicarboxylates [J].

Bang, Saet Byeol ;

Kim, Jinho .

SYNTHETIC COMMUNICATIONS, 2018, 48 (11) :1291-1298

[3] Al2O3-Supported Cu-Catalyzed Electrophilic Substitution by PhSeBr in Organoboranes, Organosilanes, and Organostannanes. A Protocol for the Synthesis of Unsymmetrical Diaryl and Alkyl Aryl Selenides [J].

Bhadra, Sukalyan ;

Saha, Amit ;

Ranu, Brindaban C. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (14) :4864-4867

[4] Synthesis and ene reactions of di-(-)-menthyl diazenedicarboxylate [J].

Brimble, MA ;

Heathcock, CH ;

Nobin, GN .

TETRAHEDRON-ASYMMETRY, 1996, 7 (07) :2007-2016

[5] ALLYLIC AMINATION BY THE LEWIS-ACID-MEDIATED ENE REACTION OF DIETHYL AZODICARBOXYLATE WITH ALKENES [J].

BRIMBLE, MA ;

HEATHCOCK, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) :5261-5263

[6] The mitsunobu reaction: Origin, mechanism, improvements, and applications [J].

But, Tracy Yuen Sze ;

Toy, Patrick H. .

CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (11) :1340-1355

[7] FISCHER REACTION OF CYCLOHEXANONE MESITYLHYDRAZONE - EVIDENCE OF A 1,4-METHYL MIGRATION [J].

CARLIN, RB ;

MOORES, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (21) :4107-&

[8] Novel Use of CF3SO2Cl for the Metal-Free Electrophilic Trifluoromethylthiolation [J].

Chachignon, Helene ;

Maeno, Mayaka ;

Kondo, Hiroya ;

Shibata, Norio ;

Cahard, Dominique .

ORGANIC LETTERS, 2016, 18 (10) :2467-2470

[9] Organocatalytic Carbon-Sulfur Bond-Forming Reactions [J].

Chauhan, Pankaj ;

Mahajan, Suruchi ;

Enders, Dieter .

CHEMICAL REVIEWS, 2014, 114 (18) :8807-8864

[10] Lewis base activation of lewis acids: Development of a Lewis base catalyzed selenolactonization [J].

Denmark, Scott E. ;

Collins, William R. .

ORGANIC LETTERS, 2007, 9 (19) :3801-3804

← 1 2 3 4 5 6 7 8 →