Perfluoroalkylation Reactions by Electron Donor‐Acceptor Complexes: Recent Advances

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

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Recent Progress in C–S Bond Formation via Electron Donor-Acceptor Photoactivation

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This review summarizes recent progress in EDA complex-promoted C–S bond formation using various sulfur-containing substrates under mild conditions via visible light irradiation.

Language: Английский

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A Dual Catalytic Approach for the Halogen-Bonding-Mediated Reductive Cleavage of α-Bromodifluoroesters and Amides

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 19, 2024

While charge-transfer complexes involving halogen-bonding interactions have emerged as an alternative strategy for the photogeneration of carbon radicals, examples using (fluoro)alkyl bromides are limited. This report describes a dual catalytic approach radical generation from α-bromodifluoroesters and amides under visible-light irradiation. Mechanistic studies suggest that reaction proceeds through in situ bromide displacement iodide salt, generating C–I bond can be engaged by our photocatalysis platform.

Language: Английский

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Electrochemical Trifluoromethylation of Alkynes: The Unique Role of DMSO as a Masking Auxiliary

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

An electrochemical trifluoromethylation method for terminal alkynes has been developed, facilitating the synthesis of CF 3 -alkynes with DMSO as a masking auxiliary.

Language: Английский

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