NH2OH-HCl-Mediated Umpolung α-Methylsulfonylation of α-Sulfonyl Ketones with Methylsulfoxides: Synthesis of α,β-Bis-sulfonyl Arylketones

被引：32
作者：
Chang, Meng-Yang [1 ,2 ]
Chen, Han-Yu [1 ]
Tsai, Yu-Lin [1 ]
机构：
[1] Kaohsiung Med Univ, Dept Med & Appl Chem, Kaohsiung 807, Taiwan
[2] Kaohsiung Med Univ Hosp, Dept Med Res, Kaohsiung 807, Taiwan
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 06期
关键词：
ONE-POT SYNTHESIS; CARBENE-CATALYZED UMPOLUNG; DIMETHYL-SULFOXIDE; 3-COMPONENT SYNTHESIS; ASYMMETRIC-SYNTHESIS; QUINOXALINES; OXIDATION; DMSO; EFFICIENT; ACCESS;
D O I：
10.1021/acs.orglett.9b00422
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In this paper, a novel and efficient route for the synthesis of alpha,beta-bis-sulfonyl arylketones via an NH2OH-HCl-mediated intermolecular umpolung alpha-methylsulfonylation of alpha-sulfonyl ketones with methylsulfoxides is described. A plausible mechanism is proposed and discussed. Various reaction conditions for this efficient, one-pot, environmentally friendly transformation were investigated.
引用
收藏
页码：1832 / 1836
页数：5
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共 73 条
[1]   Potassium hydroxide-mediated novel rearrangement of 2-alkyl-sulfonyl-2-arylsulfonyl-1-phenylethanones to 1-aryl-2-(arylsulfonylmethanesulfonyl)ethanones [J].
Bin, JK ;
Lee, JS ;
Kim, K .
ORGANIC LETTERS, 2004, 6 (23) :4297-4300
[2]   Synthesis of 1-Aryltetralins and 1-Arylnaphthalenes via (4+2) Annulation of β-Ketosulfones with Styryl Bromides [J].
Chang, Meng-Yang ;
Cheng, Yu-Chieh .
ORGANIC LETTERS, 2016, 18 (07) :1682-1685
[3]   Synthesis of Substituted Tetralins and Benzosuberans via BF3•OEt2-Mediated Formal (4+2) and (5+2) Stereocontrolled Cycloaddition of 4-Alkenols with Veratrol [J].
Chang, Meng-Yang ;
Cheng, Yu-Chieh .
ORGANIC LETTERS, 2016, 18 (03) :608-611
[4]   Bi(OTf)3 Mediated exo-Olefin Isomerization of α-Benzoyl β-Styrylsulfones [J].
Chang, Meng-Yang ;
Cheng, Yu-Chieh .
ORGANIC LETTERS, 2015, 17 (22) :5702-5705
[5]   Synthesis of Substituted Benzenes via Bi(OTf)3-Mediated Intramolecular Carbonyl Allylation of a-Prenyl or α-Geranyl β-Arylketosulfones [J].
Chang, Meng-Yang ;
Cheng, Yu-Chieh ;
Lu, Yi-Ju .
ORGANIC LETTERS, 2015, 17 (12) :3142-3145
[6]   Bi(OTf)3-Mediated Cycloisomerization of γ-Alkynyl Arylketones: Application to the Synthesis of Substituted Furans [J].
Chang, Meng-Yang ;
Cheng, Yu-Chieh ;
Lu, Yi-Ju .
ORGANIC LETTERS, 2015, 17 (05) :1264-1267
[7]   One-Pot Access to Sulfonylmethyl Arylpyrroles via the Domino Aerobic Wacker-Type Aminocyclization/1,4-Sulfonyl Migration [J].
Chang, Meng-Yang ;
Cheng, Yu-Chieh ;
Lu, Yi-Ju .
ORGANIC LETTERS, 2014, 16 (23) :6252-6255
[8]   Oxidative cleavage of α-sulfonyl ketones to carboxylic acids with Ce(NH4)2(NO3)6 [J].
Chang, Meng-Yang ;
Tsai, Chung-Yu .
TETRAHEDRON LETTERS, 2014, 55 (40) :5548-5550
[9]   Umpolung Addition of Aldehydes to Aryl Imines [J].
Chen, Ning ;
Dai, Xi-Jie ;
Wang, Haining ;
Li, Chao-Jun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (22) :6260-6263
[10]   Phosphine-Catalyzed Asymmetric Synthesis of α-Quaternary Amine via Umpolung γ-Addition of Ketimines to Allenoates [J].
Chen, Peng ;
Zhang, Junliang .
ORGANIC LETTERS, 2017, 19 (24) :6550-6553
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