Regioselective Thiol-yne Reaction of Thiol with ((Methyl-d3)sulfonyl)ethyne: Synthesis of (2-((Methyl-d3)sulfonyl)vinyl)sulfides DOI

Ji-Min Cao,

Xinyu Liu,

Weidong Rao

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 89(1), С. 363 - 372

Опубликована: Дек. 12, 2023

Herein, we have developed a new method for the synthesis of ((methyl-d3)sulfonyl)ethyne, which is cost-effective and environmentally friendly can be synthesized at gram level. As an ideal thiol-yne reagent, it reacted with various types thiols to afford (Z)- (E)-type vinyl sulfides under different conditions high selectivity. In addition, complete conformational transition from Z- E-type products suitable conditions, also carry out further derivatization smoothly. The deuterium content all was greater than 99%. preliminary mechanistic studies support visible light-mediated radical course, herein provide novel efficient synthetic strategy direct introduction deuterated methyl groups, enriching methods construction C–S bond-containing compounds.

Язык: Английский

Synthesis and applications of thiosulfonates and selenosulfonates as free-radical reagents DOI Creative Commons
Xin Wang, Jianping Meng, Dongyang Zhao

и другие.

Chinese Chemical Letters, Год журнала: 2022, Номер 34(4), С. 107736 - 107736

Опубликована: Авг. 11, 2022

Язык: Английский

Процитировано

61

Radical-mediated photoredox hydroarylation with thiosulfonate DOI

Xiaoyuan Wan,

Dahan Wang, Huawen Huang

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(19), С. 2767 - 2770

Опубликована: Янв. 1, 2023

Radical-mediated photoredox hydroarylation reaction of unactivated alkenes using thiosulfonate compounds as key radical precursors to synthesize pyridyquinazolinone and pyrroloquinazolinone derivatives is described.

Язык: Английский

Процитировано

23

Visible-Light-Driven Unsymmetric gem-Difunctionalization of Vinyl Azides with Thiosulfonates or Selenosulfonates DOI
Tao Wang,

Yuan-Yuan Zong,

Biao Yang

и другие.

Organic Letters, Год журнала: 2024, Номер 26(8), С. 1683 - 1687

Опубликована: Фев. 16, 2024

Thiosulfonylation and selenosulfonylation of vinyl azides with thiosulfonates selenosulfonates were achieved using Cu(dap)2Cl as a photosensitizer under visible-light irradiation. This reaction is the application azide substrate in group transfer radical addition (GTRA) reaction, through β-difunctionalization, to obtain variety unsymmetric difunctionalized N-unprotected enamines.

Язык: Английский

Процитировано

8

Electron Donor–Acceptor Complex Enabled Cyclization/Sulfonylation Cascade of N-Heterocycles with Thianthrenium Salts DOI

Zhengjun He,

Zhi Li,

Shuo Lai

и другие.

Organic Letters, Год журнала: 2024, Номер 26(31), С. 6652 - 6657

Опубликована: Июль 26, 2024

We report a visible-light-promoted cyclization/sulfonylation cascade of N-heterocycles with thianthrenium salts using DABSO as the SO2 surrogate. This method features excellent functional group tolerance, wide substrate scope, and late-stage elaboration bioactive relevant molecules. Mechanistic investigations reveal that photoactive electron donor–acceptor (EDA) complexes between DABCO are capable generation aryl radicals, which induce following insertion by attacking DABSO, thus triggering key radical cyclization step.

Язык: Английский

Процитировано

8

Tunable vicinal, geminal diphosphorylation and C–N bond phosphorylation of enaminones toward divergent phosphorylated ketone derivatives DOI

Dingsheng Cao,

Chaoli Wang, Jie‐Ping Wan

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(42), С. 6383 - 6386

Опубликована: Янв. 1, 2023

The tunable reactions of enaminones with phosphine oxides/phosphonates in the form vicinal- and geminal diphosphorylation, C–N bond phosphorylation have been developed, providing new methods for synthesis divergent phosphorylated molecules.

Язык: Английский

Процитировано

16

Cross-Electrophile Couplings of Benzyl Sulfonium Salts with Thiosulfonates via C–S Bond Activation DOI

Xuan-Bo Hu,

Yuwei Chen, Chenlong Zhu

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(18), С. 13601 - 13607

Опубликована: Сен. 4, 2024

A zinc-mediated cross-electrophile coupling of benzyl sulfonium salts with thiosulfonates via C-S bond cleavage was achieved. The reductive thiolation proceeded well under transition metal-free conditions to afford the desired sulfides in good yields, exhibiting both broad substrate scope and functionality tolerance. In addition, reaction could be applied use selenosulfonate as an effective selenylation agent subjected scale-up synthesis.

Язык: Английский

Процитировано

6

1,n-Thiosulfonylation using thiosulfonates as dual functional reagents DOI
Danhua Ge, Jiawei Chen, Pei Xu

и другие.

Chinese Chemical Letters, Год журнала: 2022, Номер 33(11), С. 4732 - 4739

Опубликована: Фев. 15, 2022

Язык: Английский

Процитировано

21

Metal-Free One-Pot Multi-Functionalization of Unsaturated Compounds with Interelement Compounds by Radical Process DOI Creative Commons
Yuki Yamamoto, Akiya Ogawa

Molecules, Год журнала: 2023, Номер 28(2), С. 787 - 787

Опубликована: Янв. 12, 2023

In recent years, the importance of “environmentally friendly manufacturing” has been increasing toward establishment a resource-recycling society. organic synthesis, as well, it is becoming increasingly important to develop new synthetic strategies with resource conservation and recycling elemental resources in mind, rather than just only synthesis. Many studies on construction frameworks functional molecules using ionic reactions transition-metal-catalyzed have reported, but most them focused formation carbon–carbon bonds. However, essential introduce appropriate groups at positions order for express their functions, furthermore, highly selective preparation multiple considered creation molecules. this review, we focus radical high group selectivity overview progress practical methods simultaneous introduction propose future that emphasize environmental friendliness.

Язык: Английский

Процитировано

11

Electrophotocatalytic Tellurosulfonylation of Alkynes for the Synthesis of β-(Telluro)vinyl Sulfones DOI

Zhiheng Zhao,

Huiping Zhang, Hongyan Yan

и другие.

Organic Letters, Год журнала: 2024, Номер 26(29), С. 6114 - 6119

Опубликована: Июль 5, 2024

Difunctionalization of alkynes has gained a lot interest in current organic chemistry. Herein, we developed an electrophotocatalytic multicomponent cascade reaction and indoles with sulfinic acid sodium salts using elemental tellurium as the source. Using synergistic anodic oxidation visible-light irradiation, various β-(telluro)vinyl sulfones have been prepared. This strategy features mild conditions, excellent substrate scope, readily available starting materials, great functional group tolerance.

Язык: Английский

Процитировано

4

Stainless steel-initiated thiosulfonylations of unactivated alkenes under solvent-free conditions in a mixer mill DOI

Deshen Kong,

Carsten Bolm

Green Chemistry, Год журнала: 2022, Номер 24(17), С. 6476 - 6480

Опубликована: Янв. 1, 2022

Under mechanochemical conditions in a stainless steel milling equipment, thiosulfonates react with unactivated alkenes to give the corresponding addition products high yields.

Язык: Английский

Процитировано

19