Transition-Metal-Free Allylic Defluorination Cross-Electrophile Coupling Employing Rongalite DOI Open Access
Xiang‐Long Chen, Chun‐Yan Wu, Dong‐Sheng Yang

и другие.

Authorea (Authorea), Год журнала: 2024, Номер unknown

Опубликована: Март 13, 2024

The conversion of CF3-alkenes to gem-difluoroalkenes using reductive cross-coupling strategy has received much attention in recent years, however, the use green and readily available reducing salt mediate these reactions remains be explored. In this work a concise construction gem-difluoroalkenes, which requires neither catalyst nor metal agent, was established. Rongalite, safe inexpensive industrial product, employed as both radical initiator reductant. This procedure compatible with linear cyclic diaryliodonium salts, enabling wide variety substrates (>70 examples). utility approach demonstrated through gram-scale synthesis efficient late-stage functionalizations anti-inflammatory drugs.

Язык: Английский

Chemodivergent Synthesis of Benzofurans and 2,3‐Dihydrobenzofurans via Tandem Oxidative Annulation of Enaminones and Salicylaldehydes DOI
Xiyan Duan, Hui Li, Junqi Wang

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(15), С. 1727 - 1733

Опубликована: Март 26, 2024

Comprehensive Summary Chemodivergent synthesis of benzofurans and 2,3‐dihydrobenzofurans has been realized. Under a reaction system consisting DBDMH K 2 CO 3 as promotors, controlled conditions enabled the formation two sets valuable heterocycles from tandem transformation enaminones salicylaldehydes. The key to success was identification parameters, in which imine intermediate formed by transient halogenation coupling substitution processes underwent either aldol condensation/annulation or hydrolysis/aldol condensation. additives NH 4 Cl Fe (SO ) unique selectivity this reaction. A broad substrate scope salicylaldehydes employed reaction, demonstrating excellent functional group tolerance versatility.

Язык: Английский

Процитировано

7

Photoredox Enabled Defluorinative Benzylation of Trifluoromethyl Alkenes with Alkylarenes DOI

Yutao Shi,

Jinhuan Nie,

Zhijie Wu

и другие.

Organic Letters, Год журнала: 2023, Номер 26(1), С. 100 - 105

Опубликована: Дек. 26, 2023

Herein, we report a photoredox enabled defluorinative benzylation of trifluoromethyl alkenes with readily available alkylarenes, which provides convenient access to series structurally valuable benzylated gem-difluoroalkenes under mild reaction conditions. The synthetic value this protocol has been demonstrated by the transformations several substrates bearing drug moieties, gram-scale reactions, and various further derivatizations gem-difluoroalkene products. preliminary mechanistic investigations suggest pathway rate-determining benzyl C–H bond cleavage toluene followed benzylic radical formation.

Язык: Английский

Процитировано

14

Titanium in photocatalytic organic transformations: current applications and future developments DOI
Jia‐Lin Tu, Binbin Huang

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(33), С. 6650 - 6664

Опубликована: Янв. 1, 2024

Titanium, as an important transition metal, has garnered extensive attention in both industry and academia due to its excellent mechanical properties, corrosion resistance, unique reactivity organic synthesis. In the field of photocatalysis, titanium-based compounds such titanium dioxide (TiO

Язык: Английский

Процитировано

6

Transition‐Metal‐Free Allylic Defluorination Cross‐Electrophile Coupling Employing Rongalite DOI
Xiang‐Long Chen, Chun‐Yan Wu, Dong‐Sheng Yang

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(12), С. 1360 - 1366

Опубликована: Фев. 23, 2024

Comprehensive Summary The conversion of CF 3 ‐alkenes to gem ‐difluoroalkenes using reductive cross‐coupling strategy has received much attention in recent years, however, the use green and readily available reducing salt mediate these reactions remains be explored. In this work, a concise construction gem‐ difluoroalkenes, which requires neither catalyst nor metal agent, was established. Rongalite, safe inexpensive industrial product, employed as both radical initiator reductant. This procedure compatible with linear cyclic diaryliodonium salts, enabling wide variety substrates (>70 examples). utility approach demonstrated through gram‐scale synthesis efficient late‐stage functionalizations anti‐inflammatory drugs.

Язык: Английский

Процитировано

5

Synthesis of 2‐(β‐Trifluoromethyl‐β‐arylethylthio)pyridine through DBU‐Mediated Regioselective Addition of Pyridine‐2(1H)‐thione Onto α‐(Trifluoromethyl)styrenes DOI

Pai Zheng,

Yupian Deng,

Jingjing He

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(3)

Опубликована: Янв. 8, 2024

Abstract An efficient and practical method for the synthesis of (β‐trifluoromethyl‐β‐aryl)ethyl 2‐pyridyl thioethers via hydrothiolation α‐(trifluoromethyl)styrenes with pyridine‐2(1 H )‐thione was reported. The reaction proceeded smoothly regioselectively in an anti‐Markovnikov manner assistance DBU afforded a variety trifluoromethyl‐containing moderate to good yields.

Язык: Английский

Процитировано

3

Chemodivergent alkylation of trifluoromethyl alkenes via photocatalytic coupling with alkanes DOI Creative Commons
Pol Martínez-Balart, Álvaro Velasco‐Rubio, Sergio Barbeira-Arán

и другие.

Green Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

A photocatalytic methodology for the chemodivergent direct cross-coupling of simple alkanes with trifluoromethyl alkenes that enables selective formation gem -difluoroalkenes and is presented.

Язык: Английский

Процитировано

3

Photoinduced defluorinative alkylation of trifluoromethyl alkenes with carbonyl derivatives by C–C bond scission DOI

Lu-Yu Yan,

Zhang Tianzhen,

Ze-Zhong Lv

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(24), С. 6205 - 6211

Опубликована: Янв. 1, 2023

A practical strategy for the photoinduced defluorinative alkylation of α-trifluoromethyl styrenes with carbonyl derivatives via C–C bond cleavage was disclosed.

Язык: Английский

Процитировано

8

Synthesis of gem-Difluorohomoallyl Amines via a Transition-Metal-Free Defluorinative Alkylation of Benzyl Amines with Trifluoromethyl Alkenes DOI

Man Ren,

Shengjiao Yu,

Xuefeng Li

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(12), С. 8342 - 8356

Опубликована: Май 31, 2024

A mild and transition-metal-free defluorinative alkylation of benzyl amines with trifluoromethyl alkenes is reported. The features this protocol are easy-to-obtain starting materials, a wide range substrates, functional group tolerance as well high atom economy, thus offering strategy to access variety

Язык: Английский

Процитировано

1

Photocatalyzed cascade hydrogen atom transfer for the construction of α-CF3-1,4-diketones DOI

Xiao-Ya Yuan,

Jinping Zheng, Xinyu Ma

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер unknown

Опубликована: Дек. 5, 2024

A TBADT-photocatalyzed cascade hydrogen atom transfer procedure was established for the synthesis of α-CF 3 -1,4-diketones from aldehydes and 2-bromo-3,3,3-trifluoro-1-propenes.

Язык: Английский

Процитировано

1

Iron‐Catalyzed Reductive C(aryl)—Si Cross‐Coupling of Diaryl Ethers with Chlorosilanes DOI
Pei Liu,

Baowei Wu,

Xuefeng Cong

и другие.

Chinese Journal of Chemistry, Год журнала: 2023, Номер 42(6), С. 578 - 584

Опубликована: Ноя. 7, 2023

Comprehensive Summary The reductive cross‐coupling between C(aryl)—O and Si—Cl bonds is of much importance as a valuable strategy for the construction C(aryl)—Si but has remained great challenge. Herein, we report diaryl ethers chlorosilanes via strong electrophilic cleavage by iron catalysis, which constitutes an efficient protocol synthesis range functionalized arylsilanes. combination low cost FeCl 2 precatalyst i PrMgCl reductant shows high activity in successive unactivated chlorosilanes, allowing their fashion. low‐valent species generated situ reduction with was proposed, prefers to initially bond chelation help o ‐amide auxiliary.

Язык: Английский

Процитировано

3