Indium-Catalyzed Reductive Sulfidation of Aromatic Carboxylic Acids and Aldehydes with Elemental Sulfur to Prepare Symmetrical Benzyl Sulfides

被引：12

作者：

Miyazaki, Takahiro ^{[1
]}

Nishino, Kota ^{[1
]}

Yoshimoto, Shunsuke ^{[1
]}

Ogiwara, Yohei ^{[1
]}

Sakai, Norio ^{[1
]}

机构：

[1] Tokyo Univ Sci RIKADAI, Fac Sci & Technol, Dept Pure & Appl Chem, Noda, Chiba 2788510, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 09期

关键词：

Indium; Thioethers; Carboxylic acids; Aldehydes; Sulfur; ARYL IODIDES; OXIDATIVE TRIFLUOROMETHYLTHIOLATION; CARBONYL-COMPOUNDS; COUPLING REACTIONS; BORONIC ACIDS; EFFICIENT; THIOLS; LIGAND; HALIDES; THIOETHERIFICATION;

D O I：

10.1002/ejoc.201403567

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Described herein is a direct approach to symmetrical thioethers from either aromatic carboxylic acids or aromatic aldehydes with elemental sulfur (S-8) by using a reducing system combined with InI3 and 1,1,3,3-tetramethyldisiloxane (TMDS). This sulfidation does not require functionalized sulfur reagents, such as sulfides, disulfides, or metal sulfides, and it simultaneously forms two carbon-sulfur bonds in a single catalytic system.

引用

页码：1991 / 1994

页数：4

共 11 条

[1] Indium-Catalyzed Reductive Sulfidation of Esters by Using Thiols: An Approach to the Diverse Synthesis of Sulfides
Miyazaki, Takahiro
Kasai, Shinsei
Ogiwara, Yohei
Sakai, Norio
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (05) : 1043 - 1049
[2] Indium-Catalyzed Reductive Bromination of Carboxylic Acids Leading to Alkyl Bromides
Moriya, Toshimitsu
Yoneda, Shinichiro
Kawana, Keita
Ikeda, Reiko
Konakahara, Takeo
Sakai, Norio
ORGANIC LETTERS, 2012, 14 (18) : 4842 - 4845
[3] One-pot two-step conversion of aromatic carboxylic acids and esters to aromatic aldehydes via indium-catalyzed reductive thioacetalization and desulfurization
Sakai, Norio
Minato, Kohei
Ogiwara, Yohei
TETRAHEDRON LETTERS, 2017, 58 (48) : 4563 - 4567
[4] Indium-Catalyzed Reductive Esterification of a Carboxylic Acid: Sequential Preparation of an Ester and Symmetrical Ether
Sakai, Norio
Usui, Yuta
Ikeda, Reiko
Konakahara, Takeo
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (18) : 3397 - 3401
[5] Single-Step Thioetherification by Indium-Catalyzed Reductive Coupling of Carboxylic Acids with Thiols
Sakai, Norio
Miyazaki, Takahiro
Sakamoto, Tomohiro
Yatsuda, Takuma
Moriya, Toshimitsu
Ikeda, Reiko
Konakahara, Takeo
ORGANIC LETTERS, 2012, 14 (17) : 4366 - 4369
[6] Indium-catalyzed reductive three-component coupling reaction of aliphatic/aromatic carboxylic acids with t-butyl mercaptan leading to unsymmetrical dialkyl sulfides
Sakai, Norio
Yoshimoto, Shunsuke
Miyazaki, Takahiro
Ogiwara, Yohei
TETRAHEDRON LETTERS, 2016, 57 (29) : 3117 - 3120
[7] INDIUM(III)-CATALYZED REDUCTIVE ONE-POT SYNTHESIS OF THIOETHERS FROM AROMATIC ALDEHYDES AND ELEMENTAL SULFUR
Miyazaki, Takahiro
Nishino, Kota
Konakahara, Takeo
Sakai, Norio
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2015, 190 (08) : 1378 - 1379
[8] Indium-catalyzed direct preparation of dibenzyl sulfides from benzyl alcohols and elemental sulfur with a hydrosilane and its application to the preparation of dibenzyl selenide
Miyazaki, Takahiro
Katayama, Masahiro
Yoshimoto, Shunsuke
Ogiwara, Yohei
Sakai, Norio
TETRAHEDRON LETTERS, 2016, 57 (06) : 676 - 679
[9] Indium-catalyzed Direct Conversion of Dibenzyl Ethers to Dibenzyl Sulfides Using Elemental Sulfur and a Hydrosilane and Its Application to the Preparation of Benzyl Selenides
Sakai, Norio
Takada, Koji
Katayama, Masahiro
Ogiwara, Yohei
CHEMISTRY LETTERS, 2018, 47 (06) : 791 - 793
[10] Indium-Catalyzed Reductive Dithioacetalization of Carboxylic Acids with Dithiols: Scope, Limitations, and Application to Oxidative Desulfurization
Nishino, Kota
Minato, Kohei
Miyazaki, Takahiro
Ogiwara, Yohei
Sakai, Norio
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (07): : 3659 - 3665

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