Switchable Nucleophilic Site Enables Expedient Synthesis of CF3-Containing Thiazoles and Allenes from 1,3-Enynes DOI
Xiangyu Li, Na Li, Lan Yang

и другие.

ACS Catalysis, Год журнала: 2023, Номер 13(19), С. 12755 - 12765

Опубликована: Сен. 15, 2023

Typically, trimethylsilyl isothiocyanate (TMSNCS) is used as a nucleophilic thiocyanate building block (−S–C≡N) that reacts with various electrophiles. However, it has been less explored source of isothiocyanates (−N═C═S), which can usually be converted by thermal isomerization allyl or propargyl thiocyanates. Achieving method precise site control even more challenging. Here, we demonstrate an approach uses metal catalysts to switchable sites and provide strategy construct CF3-containing thiazoles allenes via the multicomponent reaction 1,3-enynes, TMSNCS, electrophilic trifluoromethyl reagent. In presence inexpensive Fe(III) Cu(II) catalysts, current practical convenient, compatible substrates bearing sensitive functional groups readily transferred complex scaffolds. The biological evaluation showed two developed exhibited dramatic inhibitory activities for three human cancer cell lines beyond those 5-fluorouracil. Both compounds increased level reactive oxygen species in MCF-7 cells, believed early step tumor apoptosis.

Язык: Английский

A straightforward access to trifluoromethylated natural products through late-stage functionalization DOI
Heping Li, Xiang‐Hong He, Cheng Peng

и другие.

Natural Product Reports, Год журнала: 2022, Номер 40(5), С. 988 - 1021

Опубликована: Окт. 7, 2022

This review summarizes the applications of late-stage strategies in direct trifluoromethylation natural products past ten years, with particular emphasis on reaction model each method.

Язык: Английский

Процитировано

28
Electrochemically Induced Regio‐ and Stereoselective (E)‐β‐C(sp2)−H Trifluoromethylation and Arylsulfonylation of Enamides DOI

Fukuan Zhang,

Xuefei Zhao, Jie Zhang

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(23), С. 4036 - 4042

Опубликована: Ноя. 1, 2022

Abstract Herein, we disclosed an electrochemically induced method for the regio‐ and stereoselective ( E )‐β‐C( sp 2 )−H trifluoromethylation of enamides by employing readily available inexpensive Langlois’ reagent (CF 3 SO Na). Preliminary mechanistic studies indicate involvement free radicals in process. The exogenous oxidant‐free reaction proceeds undivided electrochemical cell under mild conditions allows accomplishment products with exclusive ‐selective control. methodology is featured catalyst‐free, simple setup, broad substrate scopes good functional group tolerance. Using ArSO Na as coupling partner, corresponding arylsulfonylated are obtained standard conditions. magnified image

Язык: Английский

Процитировано

25
Spotting Trends in Organocatalyzed and Other Organomediated (De)polymerizations and Polymer Functionalizations DOI Creative Commons
M.A. del Valle, Marta Ximenis, Xabier Lopez de Pariza

и другие.

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(36)

Опубликована: Июнь 14, 2022

Abstract Organocatalysis has evolved into an effective complement to metal‐ or enzyme‐based catalysis in polymerization, polymer functionalization, and depolymerization. The ease of removal greater sustainability organocatalysts relative transition‐metal‐based ones spurred development specialty applications, e.g., medical devices, drug delivery, optoelectronics. Despite this, the use organocatalysis other organomediated reactions chemistry is still rapidly developing, we envisage their growing application nascent areas such as controlled radical additive manufacturing, chemical recycling coming years. In this Review, describe ten trending where anticipate paradigm shifts resulting from novel transition‐metal‐free conditions. We highlight opportunities challenges detail how new discoveries could lead previously inaccessible functional materials a potentially circular plastics economy.

Язык: Английский

Процитировано

23
Electrocatalytic synthesis: an environmentally benign alternative for radical-mediated aryl/alkenyl C(sp2)–C(sp3) cross-coupling reactions DOI
Mu‐Jia Luo, Haixin Ding,

Ruchun Yang

и другие.

Green Chemistry, Год журнала: 2022, Номер 24(24), С. 9373 - 9401

Опубликована: Янв. 1, 2022

This review covers the recent progress in electrochemically enabled radical-mediated aryl/alkenyl C(sp 2 )–C(sp 3 ) cross-coupling reactions, including synthetic strategies, plausible mechanisms and further research outlook.

Язык: Английский

Процитировано

23
Switchable Nucleophilic Site Enables Expedient Synthesis of CF3-Containing Thiazoles and Allenes from 1,3-Enynes DOI
Xiangyu Li, Na Li, Lan Yang

и другие.

ACS Catalysis, Год журнала: 2023, Номер 13(19), С. 12755 - 12765

Опубликована: Сен. 15, 2023

Typically, trimethylsilyl isothiocyanate (TMSNCS) is used as a nucleophilic thiocyanate building block (−S–C≡N) that reacts with various electrophiles. However, it has been less explored source of isothiocyanates (−N═C═S), which can usually be converted by thermal isomerization allyl or propargyl thiocyanates. Achieving method precise site control even more challenging. Here, we demonstrate an approach uses metal catalysts to switchable sites and provide strategy construct CF3-containing thiazoles allenes via the multicomponent reaction 1,3-enynes, TMSNCS, electrophilic trifluoromethyl reagent. In presence inexpensive Fe(III) Cu(II) catalysts, current practical convenient, compatible substrates bearing sensitive functional groups readily transferred complex scaffolds. The biological evaluation showed two developed exhibited dramatic inhibitory activities for three human cancer cell lines beyond those 5-fluorouracil. Both compounds increased level reactive oxygen species in MCF-7 cells, believed early step tumor apoptosis.

Язык: Английский

Процитировано

15