Halogen-bond-assisted radical remote difunctionalization of bicyclo[1.1.1]butane skeleton DOI
Hui Liu, Zhenda Fu, Xingwei Li

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Transition-metal-free radical remote difunctionalization of bicyclo[1.1.1]butane skeletons in both two- and three-component fashions is presented.

Language: Английский

Perfluoroalkylation Reactions by Electron Donor‐Acceptor Complexes: Recent Advances DOI
Damian E. Yerien, Sebastián Barata‐Vallejo, Al Postigo

et al.

ChemPhotoChem, Journal Year: 2024, Volume and Issue: 8(8)

Published: May 3, 2024

Abstract This Perspective analyses the perfluoroalkylation reactions by electron donor‐acceptor (EDA) complexes since 2018, while summarizes, in Tables , vast majority of representative various classes organic compounds EDA and halogen‐bonding interactions. Numerous intriguing reaction methodologies valuable synthetic instances have emerged. We aim to delve into these new examples comprehensively, also contemplating future directions field. Subsequent sections will elaborate on (hetero)aromatic compounds, carbon‐carbon multiple bonds, carbonyl isocyanides, covering their scope mechanistic insights. Perfluoroalkylation complexes. Entry Substrate Complex Reaction conditions Product Ref. 1 [13] 2 [46] 3 R F I (3 equiv.) KOH (1.5 Blue LEDs H O, Ar, 20 h [47] 4 TEEDA CFL (25 W) THF, r.t. F− [48] 5 ICF CO Et (1.3 Na DMSO mL) rt. 427 nm LED, 16 [49] 6 TMG (2.5 23 W CFL, MeCN/Hex f (5 : 1) [42,50] 7 MeCN [51] 8 Umemoto's reagent (2 N ‐methylmorpholine DMF, [52] 9 Cs white light O r.t., [53] 10 4.5 450 laser CaCl MeNO 0 °C [3] 11 t ‐BuONa DMF Green [54] 12 or complex I−R (2.1 TMEDA DBU 24 [55,56] 13 TFE/water (1 (0.2 M) CF SO [84] bonds constrained cyclic Bu NCl, Hg lamp (6 (1.2 CH OH, 1.5 r.t, Ar [39] [57] DIPEA …….. −I Base THF 25 with DIPEA, TEEDA; [48,58,59] Bn NH [60] Base, [61] O/toluene=9 LEDs, 65 °C, [41] K PO CuCl (10 mol%) TMSNCS CN Violet (24 [37] Diphenylacetaldehyde Pyrrolidine (40 DCE mL); (0.8 eq.); White W); [44,62] DIPEA,DMA (trace air) 36–72 [63] n ‐C air, RT [64] DABCO υ (400 Watt) 50 C 2n+1 (1.8 [65–67] DCE, [27] 14 2,4,6‐trimethylpyridine MeCN, 60 Togni's [68] 15 PMDETA [69] [70,71] 17 less than % water mmol) isocyanides hydrazones. [72,73] cis ‐catalyst M (20 2,6‐lutidine (0.7 ‐10 [74] [75] phase transfer catalyst Cl/8F 18 1), [32] ambient NaOH (4.1 R.T. [76] 36 30 [77] I−C [78] [79] Imidazole [80]

Language: Английский

Citations

5
Photoinduced selective perfluoroalkylation of terminal alkynes via electron donor–acceptor complexes DOI
Xiaolin Shi, Bo Yu, Xin Zhou

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(18), P. 2532 - 2535

Published: Jan. 1, 2024

An efficient photocatalytic method was developed for selective perfluoroalkylation of terminal alkynes via in-situ generated EDA complexes derived from a thymol anion and perfluoroalkyl iodides.

Language: Английский

Citations

4
Base-induced azofluoroalkylation of unactivated alkenes via halogen atom transfer DOI
Jing Zhang,

Yanchuang Zhao,

Yu-Yi Zhu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(8), P. 2161 - 2170

Published: Jan. 1, 2024

A base-induced three-components coupling employing unactivated alkenes, fluoroalkyl iodides and diazonium salts under mild reaction conditions has been developed.

Language: Английский

Citations

4
Development of heterogeneous palladium catalyst for perfluoroalkylative carbonylation of alkenes with alkyl halides DOI
Shuyu Yang, Bo Zhang, Heng Yang

et al.

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 573, P. 114803 - 114803

Published: Jan. 6, 2025

Language: Английский

Citations

0
Nickel-Catalyzed Synthesis of Fluorine-Bearing Silane through Halofluoroalkylation and Hydrofluoroalkylation of Alkenylsilanes DOI Creative Commons
Ting Su, Heng Wang, Wenxin Lu

et al.

Tetrahedron Chem, Journal Year: 2025, Volume and Issue: unknown, P. 100129 - 100129

Published: April 1, 2025

Language: Английский

Citations

0
Study of tamoxifen derived perfluoroalkylated olefins in breast cancer treatment DOI Creative Commons
Wojciech Chaładaj, María C. Arufe, Fátima Lucio‐Martínez

et al.

Bioorganic Chemistry, Journal Year: 2025, Volume and Issue: 161, P. 108525 - 108525

Published: April 25, 2025

Language: Английский

Citations

0
Energy Transfer Catalysis Enabled 2,2,2‐Trifluoroethoxy‐Amination of Olefins DOI Creative Commons
Floriane Doche, Thibault Gallavardin, Thomas Poisson

et al.

ChemistryEurope, Journal Year: 2025, Volume and Issue: unknown

Published: May 6, 2025

A thioxanthone‐catalyzed 2,2,2‐trifluoroethoxyamination of olefins is developed via the formation corresponding alkoxy and iminyl radicals using unprecedented, easily prepared, bench‐stable oxime ethers as bifunctional reagents. To bypass possible side reactions (1,2‐Hydrogen Atom Transfer (HAT), H‐abstraction, β‐scission), high reactivity radical fine‐tuned to promote selective challenging a COCH 2 CF 3 bond. This reaction, involving triplet energy transfer process, allows concomitant CN COAlk bond, so far uncharted, ether Hence, difunctionalization myriad electron‐rich alkenes selectively afforded anti‐Markovnikov products with large functional group tolerance (44 examples, up 77% yield), offering straightforward complementary regioselectivity compared existing approaches for 2,2,2‐trifluoroethanol. Post‐functionalization mechanistic investigations provided key insights into reaction mechanism this transformation.

Language: Английский

Citations

0
Modulating β‐Keto‐enamine‐Based Covalent Organic Frameworks for Photocatalytic Atom‐Transfer Radical Addition Reaction DOI

Yuting Zhao,

Lei Li,

Jiyuan Zang

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(24)

Published: Feb. 26, 2024

The atom-transfer radical addition (ATRA) reaction simultaneously forges carbon-carbon and carbon-halogen bonds. However, frequently-used photosensitizers such as precious transition metal complexes, or organic dyes have limitations in terms of their potential toxicity recyclability. Three β-ketoenamine-linked covalent frameworks (COFs) from 1,3,5-triformylphloroglucinol 1,4-phenylenediamines with variable transient photocurrent photocatalytic activity been prepared. A COF bearing electron-deficient Cl atoms displayed the highest toward ATRA polyhalogenated alkanes to give halogenated olefins under visible light at room temperature. This heterogeneous photocatalyst exhibited good functional group tolerance could be recycled without significant loss activity.

Language: Английский

Citations

3
A general Fe-catalysed azidation of iododifluoroketones and its utilization for the synthesis of gem-difluoromethylenated triazoles DOI
Xia Wang,

Shixun Liu,

Shibo Xu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 2054 - 2061

Published: Jan. 1, 2024

An iron-catalysed radical azidation of iododifluoroketones with TMSN 3 was developed under mild conditions to provide a concise synthesis α-difluoroalkylazides, which could be transformed into the useful N–CF 2 triazoles via CuAAC reaction.

Language: Английский

Citations

2
Regioselective difunctionalization of alkenes with CF2FG Moieties DOI Creative Commons
Thomas Castanheiro, Tatiana Besset

Journal of Fluorine Chemistry, Journal Year: 2024, Volume and Issue: 277, P. 110296 - 110296

Published: May 31, 2024

The organofluorine chemistry field has steadily increased over the years. In particular, difunctionalization of unsaturated compounds is an efficient pathway toward formation regioselective and highly functionalized aliphatic compounds. This review depicts recent advances made for simultaneously forming C−FG1 C−CF2FG2 on alkenes (FG = functional group) by catalysis. highlights approaches involving transition metal-catalyzed transformations one electron manifold.

Language: Английский

Citations

2