PhI(OAc)2/KI-Mediated Reaction of Aryl Sulfinates with Alkenes, Alkynes, and α,β-Unsaturated Carbonyl Compounds: Synthesis of Vinyl Sulfones and β-Iodovinyl Sulfones

被引：114

作者：

Katrun, Praewpan ^{[1
,2
]}

Chiampanichayakul, Supanimit ^{[1
,2
]}

Korworapan, Kanokwan ^{[1
,2
]}

Pohmakotr, Manat ^{[1
,2
]}

Reutrakul, Vichai ^{[1
,2
]}

Jaipetch, Thaworn ^{[3
]}

Kuhakarn, Chutima ^{[1
,2
]}

机构：

[1] Mahidol Univ, Fac Sci, Dept Chem, Bangkok 10400, Thailand

[2] Mahidol Univ, Fac Sci, Ctr Innovat Chem, PERCH, Bangkok 10400, Thailand

[3] Mahidol Univ, Saiyok 71150, Kanchanaburi, Thailand

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 29期

关键词：

Alkynes; Alkenes; Iodine; Sulfur; HYPERVALENT IODINE REAGENTS; ONE-POT SYNTHESIS; CONVENIENT SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; STEREOCONTROLLED SYNTHESIS; OXIDATIVE CONVERSION; SELECTIVE OXIDATION; EFFICIENT REAGENTS; MICHAEL REACTIONS; MEDIATED REACTION;

D O I：

10.1002/ejoc.201000641

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(Diacetoxyiodo)benzene [PhI(OAc)(2), DIB] was able to promote the reaction of sodium aryl sulfinate and potassium iodide (KI) with alkenes and alkynes to afford the corresponding vinyl sulfones and beta-iodovinyl sulfones, respectively, in good yields. The salient features of this reaction are that it employs a commercially available and environmentally benign hypervalent iodine(III) reagent, a one-step reaction, a short reaction time, and mild reaction conditions.

引用

页码：5633 / 5641

页数：9

共 14 条

[1] CAN mediated reaction of aryl sulfinates with alkenes and alkynes:: Synthesis of vinyl sulfones, β-iodovinyl sulfones and acetylenic sulfones
Nair, V
Augustine, A
Suja, TD
[J]. SYNTHESIS-STUTTGART, 2002, (15): : 2259 - 2265
[2] An Efficient Synthesis of Vinyl Sulfones from Alkenes and Aryl Sulfinates
Das, Biswanath
Lingaiah, Maram
Damodar, Kongara
Bhunia, Nisith
[J]. SYNTHESIS-STUTTGART, 2011, (18): : 2941 - 2944
[3] PhI(OAc)2 mediated decarboxylative sulfonylation of β-aryl-α,β-unsaturated carboxylic acids: a synthesis of (E)-vinyl sulfones
Katrun, Praewpan
Hlekhlai, Sornsiri
Meesin, Jatuporn
Pohmakotr, Manat
Reutrakul, Vichai
Jaipetch, Thaworn
Soorukram, Darunee
Kuhakarn, Chutima
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (16) : 4785 - 4794
[4] Synthesis of (E)-β-Iodovinyl Sulfones via HI-mediated Vicinal Iodosulfonylation of Alkynes with Sodium Sulfinates
Chen, Zu-Jia
Zeng, Yu
Li, Zhong-Hao
Li, Huan-Qing
Yu, Shi-Wei
Shen, Qing
Wang, Zhao-Yang
[J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 13 (06)
[5] I2/TBHP-mediated reaction of sulfonylhydrazides with alkynes: synthesis of (E)-β-iodovinyl sulfones
Li, Xiaoqing
Xu, Xiangsheng
Shi, Xinhua
[J]. TETRAHEDRON LETTERS, 2013, 54 (24) : 3071 - 3074
[6] Transition-metal-free NaI-mediated reaction of aryl sulfonyl chloride with alkynes: Synthesis of (E)-β-iodovinyl sulfones
Chen, Dan
Lin, Li
Peng, Xiaoyan
Yu, Xinyi
Yang, Zhonglie
Liu, Yutong
Zhang, Xiaobin
Li, Jiahong
Jiang, Hezhong
[J]. TETRAHEDRON LETTERS, 2021, 75
[7] Visible Light-Mediated Metal-Free Synthesis of Vinyl Sulfones from Aryl Sulfinates
Meyer, Andreas Uwe
Jaeger, Stefanie
Hari, Durga Prasad
Koenig, Burkhard
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (09) : 2050 - 2054
[8] PhI(OAc)2-mediated decomposition of N-arylsulfonyl hydrazones: metal-free synthesis of (E)-vinyl sulfones
Luo, Zaigang
Fang, Yuyu
Zhao, Yu
Xu, Xuemei
Feng, Chengtao
Li, Zhong
Zhang, Xiaomei
He, Jie
[J]. TETRAHEDRON LETTERS, 2016, 57 (36) : 4105 - 4108
[9] Chemoselective Synthesis of Unsymmetrical Internal Alkynes or Vinyl Sulfones via Palladium-Catalyzed Cross-Coupling Reaction of Sodium Sulfinates with Alkynes
Xu, Yanli
Zhao, Jinwu
Tang, Xiaodong
Wu, Wanqing
Jiang, Huanfeng
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (09) : 2029 - 2039
[10] Mn(OAc)3-Mediated Unexpected Cycloannulative Sulfonyl Migration Cascade using (E)-?-Iodovinyl Sulfones and ortho-Alkynylphenols for Direct Synthesis of Chromene-Derived Vinyl Sulfones
Reddy, Raju Jannapu
Kumar, Jangam Jagadesh
Kumari, Arram Haritha
[J]. ORGANIC LETTERS, 2023, 25 (13) : 2207 - 2212

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