Catalytic site-specific and regioselective (3+2) transannulations between 1,2,3-thiadiazoles and allenoates

被引：10

作者：

Chen, Cunzhi ^{[1
]}

Fang, Shuyan ^{[1
]}

Yu, Mingwu ^{[2
]}

Xu, Jiaxi ^{[1
]}

Yang, Zhanhui ^{[1
]}

机构：

[1] Beijing Univ Chem Technol, Coll Chem, Dept Organ Chem, Beijing 100029, Peoples R China

[2] Ludong Univ, Sch Chem & Mat Sci, Yantai 264025, Shandong, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 03期

基金：

中国国家自然科学基金;

关键词：

ALKENES; ALLENES;

D O I：

10.1039/d2qo01662a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allenoates, a type of perpendicularly "strained" surrogate of alkynes, readily transannulate, site-specifically and regio-selectively, with 1,2,3-thiadiazoles in the presence of catalytic Rh(i)/bisphosphine, producing tetrasubstituted thiophenes in a redox-neutral manner. 1,2,3-Thiadiazoles act as masked 1,3-dipoles with nucleophilic sulfur and electrophilic carbon termini.

引用

页码：661 / 667

页数：7

共 29 条

[1] Recent strategies in the synthesis of thiophene derivatives: highlights from the 2012-2020 literature [J].

Abedinifar, Fahimeh ;

Babazadeh Rezaei, Elham ;

Biglar, Mahmood ;

Larijani, Bagher ;

Hamedifar, Halleh ;

Ansari, Samira ;

Mahdavi, Mohammad .

MOLECULAR DIVERSITY, 2021, 25 (04) :2571-2604

[2] Synthesis and Applications of Thiophene Derivatives as Organic Materials [J].

Barbarella, G. ;

Zangoli, M. ;

Di Maria, F. .

ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 123, 2017, 123 :105-167

[3] Mechanistic Understanding of Transition-Metal-Catalyzed Olefin Isomerization: Metal-Hydride Insertion-Elimination vs. π-Allyl Pathways [J].

Biswas, Soumik .

COMMENTS ON INORGANIC CHEMISTRY, 2015, 35 (06) :301-331

[4] Catalytic Diastereospecific and Enantioselective (3+2) Transannulations of 1,2,3-Thiadiazoles with Strained Norbornene Derivatives [J].

Chen, Cunzhi ;

Fang, Shuyan ;

Dong, Ziyang ;

Xu, Jiaxi ;

Yang, Zhanhui .

ORGANIC LETTERS, 2022, 24 (11) :2110-2114

[5] Catalytic (3+2) umpolung annulations of α-thioacyl carbenes with aryl isothiocyanates [J].

Dong, Ziyang ;

Ma, Meng-Yao ;

Xu, Jiaxi ;

Yang, Zhanhui .

CHEMICAL COMMUNICATIONS, 2022, 58 (57) :7980-7983

[6] Dual roles of bisphosphines and epoxides: Rh-catalyzed highly chemoselective and diastereoselective (3+2) transannulations of 1,2,3-thiadiazoles with cyanoepoxides [J].

Dong, Ziyang ;

Chen, Cunzhi ;

Wang, Jing ;

Xu, Jiaxi ;

Yang, Zhanhui .

ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (23) :6687-6698

[7] Site-Selectivity Control in Organic Reactions: A Quest To Differentiate Reactivity among the Same Kind of Functional Groups [J].

Huang, Zhongxing ;

Dong, Guangbin .

ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (03) :465-471

[8]

Kamboj A., 2012, J PHARM RES, V5, P2676

[9] Highly Z-Selective Double Bond Transposition in Simple Alkenes and Allylarenes through a Spin-Accelerated Allyl Mechanism [J].

Kim, Daniel ;

Pillon, Guy ;

DiPrimio, Daniel J. ;

Holland, Patrick L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (08) :3070-3074

[10] Rhodium-Catalyzed Intramolecular Transannulation Reaction of Alkynyl Thiadiazole Enabled 5,n-Fused Thiophenes [J].

Kim, Ji Eun ;

Lee, Jinsub ;

Yun, Hyunsik ;

Baek, Yonghyeon ;

Lee, Phil Ho .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (03) :1437-1447

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