B2cat2-Mediated Reduction of Sulfoxides to Sulfides

被引：14

作者：

Takahashi, Fumiya ^{[1
]}

Nogi, Keisuke ^{[1
]}

Yorimitsu, Hideki ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 20期

关键词：

Bis(catecholato)diboron; Chemoselectivity; Reduction; Sulfide; Sulfoxide; METAL-FREE REDUCTION; PYRIDINE-N-OXIDES; EFFICIENT DEOXYGENATION; PUMMERER REACTION; CHEMOSELECTIVE REDUCTION; ORGANOSULFUR COMPOUNDS; PHOSPHORUS-COMPOUNDS; ASYMMETRIC-SYNTHESIS; BOND-CLEAVAGE; MILD;

D O I：

10.1002/ejoc.202000222

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and operationally simple method for the reduction of sulfoxides to sulfides has been developed using bis(catecholato)diboron (B(2)cat(2)) as a reducing agent. The present method accommodates various functional groups which are generally prone to reduction: halides, alkynes, carbonyls, nitriles, and heterocycles are totally intact, and only sulfoxide moieties undergo reduction chemoselectively. Moreover, the remaining diboron and the resulting boron-containing wastes are readily removable, the practicality of this protocol being thus demonstrated.

引用

页码：3009 / 3012

页数：4

共 50 条

[31] ANTIMICROBIAL NITROIMIDAZOLYL-2-SULFIDES,NITROIMIDAZOLYL-2-SULFOXIDES, AND NITROIMIDAZOLYL-2 SULFONES
TWEIT, RC
KREIDER, EM
MUIR, RD
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1973, : 48 - &
[32] NaSH-HCl mediated reduction of sulfoxides into sulfides under organic solvent-free reaction conditions
Zupanc, Anze
Jereb, Marjan
GREEN CHEMISTRY LETTERS AND REVIEWS, 2020, 13 (04) : 77 - 84
[33] Tertiary amine mediated aerobic oxidation of sulfides into sulfoxides by visible-light photoredox catalysis on TiO2
Lang, Xianjun
Hao, Wei
Leow, Wan Ru
Li, Shuzhou
Zhao, Jincai
Chen, Xiaodong
CHEMICAL SCIENCE, 2015, 6 (08) : 5000 - 5005
[34] MILD AND EFFICIENT DEOXYGENATION OF SULFOXIDES TO SULFIDES WITH CP2TiCl2/GALLIUM SYSTEM
Yoo, Byung Woo
Min, Sang Ki
SYNTHETIC COMMUNICATIONS, 2011, 41 (20) : 2993 - 2996
[35] Catalytic dehydrogenation of amines to imines and the in-situ reduction of sulfoxides into sulfides
Liu, Xixi
Wang, Yanxin
Li, Bo
Liu, Bing
Wang, Wei
Xiang, Nian
Zhang, Zehui
JOURNAL OF CATALYSIS, 2021, 401 : 81 - 88
[36] BRIDGED POLYNUCLEAR BIS(2,2-DICHLOROVINYL)SULFIDES, SULFOXIDES AND SULFONES
MARTYNOV, AV
MIRSKOVA, AN
MOSKVICHEV, YA
ZHURNAL ORGANICHESKOI KHIMII, 1993, 29 (03): : 502 - 504
[37] SYNTHESIS AND SPECTRAL STUDIES OF SOME NEW SULFIDES, SULFOXIDES, AND SULFONES .2.
KASSEM, AA
ELBARDAN, AA
MANSOUR, EME
JOURNAL OF CHEMICAL AND ENGINEERING DATA, 1987, 32 (04): : 483 - 485
[38] B(C6F5)3-Catalyzed Reduction of Sulfoxides and Sulfones to Sulfides with Hydrosilanes
Porwal, Digvijay
Oestreich, Martin
SYNTHESIS-STUTTGART, 2017, 49 (20): : 4698 - 4702
[39] Reduction of sulfoxides with boranes catalyzed by MoO2Cl2
Fernandes, Ana C.
Romao, Carlos C.
TETRAHEDRON LETTERS, 2007, 48 (52) : 9176 - 9179
[40] Electrochemically mediated enantioselective reduction of chiral sulfoxides
Chen, Kuan-I.
Challinor, Victoria L.
Kielmann, Linda
Sharpe, Philip C.
De Voss, James J.
Kappler, Ulrike
McEwan, Alastair G.
Bernhardt, Paul V.
JOURNAL OF BIOLOGICAL INORGANIC CHEMISTRY, 2015, 20 (02): : 395 - 402

← 1 2 3 4 5 →