Simple and Efficient Synthesis of Allyl Sulfones through Cs2CO3- Mediated Radical Sulfonylation of Morita-Baylis-Hillman Adducts with Thiosulfonates

被引：17

作者：

Shankar, Angothu ^{[1
]}

Waheed, Md. ^{[1
]}

Reddy, Raju Jannapu ^{[1
]}

机构：

[1] Osmania Univ, Univ Coll Sci, Dept Chem, Hyderabad 500007, Telangana, India

来源：

SYNOPEN | 2021年 / 05卷 / 01期

关键词：

allyl sulfones; cesium carbonate; MBH adducts; radical sulfonylation; thiosulfonates; STEREOSELECTIVE-SYNTHESIS; THIYL RADICALS; ACETATES; ARYL; FACILE; BOND; THIOSULFONYLATION; STRAIGHTFORWARD; ISOMERIZATION; THERMOLYSIS;

D O I：

10.1055/a-1422-9411

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient and eco-friendly method has been developed for the synthesis of allyl sulfones using Morita-Baylis-Hillman (MBH) adducts and thiosulfonates under mild conditions. The Cs2CO3-promoted radical sulfonylation provided a series of ally! sulfones in good to high yields with high stereoselectivities. A wide variety of MBH bromides/acetates as well as thiosulfonates were tolerated and reliable in scaled-up synthesis. A plausible mechanism is proposed to rationalize the radical sulfonylation.

引用

页码：91 / 99

页数：9

共 81 条

[1]

Basavaiah D, 2000, SYNTHESIS-STUTTGART, P545

[2]

Basavaiah D., 2019, J SCI RES BANARAS HI, V63, P169

[3] An expedient, facile and simple one-pot synthesis of 2-methylenealkanoates and alkanenitriles from the Baylis-Hillman bromides in aqueous media [J].

Basavaiah, Deevi ;

Reddy, Kanumuri Ramesh ;

Kumaragurubaran, Nagaswamy .

NATURE PROTOCOLS, 2007, 2 (11) :2665-2676

[4] The Baylis-Hillman reaction: a novel source of attraction, opportunities, and challenges in synthetic chemistry [J].

Basavaiah, Deevi ;

Rao, Kalapala Venkateswara ;

Reddy, Raju Jannapu .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (10) :1581-1588

[5] The Baylis-Hillman reaction: a new continent in organic chemistry - our philosophy, vision and over three decades of research [J].

Basavaiah, Deevi ;

Naganaboina, Ram Tilak .

NEW JOURNAL OF CHEMISTRY, 2018, 42 (17) :14036-14066

[6] Recent Contributions from the Baylis-Hillman Reaction to Organic Chemistry [J].

Basavaiah, Deevi ;

Reddy, Bhavanam Sekhara ;

Badsara, Satpal Singh .

CHEMICAL REVIEWS, 2010, 110 (09) :5447-5674

[7] Hydroxy-assisted catalyst-free Michael addition-dehydroxylation of Baylis-Hillman adducts in poly(ethylene glycol) [J].

Chandrasekhar, S ;

Saritha, B ;

Jagadeshwar, V ;

Narsihmulu, C ;

Vijay, D ;

Sarma, GD ;

Jagadeesh, B .

TETRAHEDRON LETTERS, 2006, 47 (17) :2981-2984

[8] ELECTRON-SPIN RESONANCE STUDIES OF RADICALS FORMED DURING THE THERMOLYSIS AND PHOTOLYSIS OF SULFOXIDES AND THIOLSULFONATES [J].

CHATGILIALOGLU, C ;

GILBERT, BC ;

GILL, B ;

SEXTON, MD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1980, (07) :1141-1150

[9] Visible-Light-Induced Cyclization/Aromatization of 2-Vinyloxy Arylalkynes: Synthesis of Thio-Substituted Dibenzofuran Derivatives [J].

Chen, Hui ;

Yan, Yunyun ;

Zhang, Niuniu ;

Mo, Zuyu ;

Xu, Yanli ;

Chen, Yanyan .

ORGANIC LETTERS, 2021, 23 (02) :376-381

[10] aza-Baylis-Hillman Reaction [J].

Declerck, Valerie ;

Martinez, Jean ;

Lamaty, Frederic .

CHEMICAL REVIEWS, 2009, 109 (01) :1-48

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