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

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(19), P. 12755 - 12765

Published: Sept. 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.

Language: Английский

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

et al.

Natural Product Reports, Journal Year: 2022, Volume and Issue: 40(5), P. 988 - 1021

Published: Oct. 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.

Language: Английский

Citations

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

Fukuan Zhang,

Xuefei Zhao, Jie Zhang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(23), P. 4036 - 4042

Published: Nov. 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

Language: Английский

Citations

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

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(36)

Published: June 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.

Language: Английский

Citations

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

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(24), P. 9373 - 9401

Published: Jan. 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.

Language: Английский

Citations

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

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(19), P. 12755 - 12765

Published: Sept. 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.

Language: Английский

Citations

15