Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 123 - 173
Published: Jan. 1, 2024
Language: Английский
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(4), P. 2144 - 2150
Published: Jan. 25, 2024
The modular four-component carbonylation of unsaturated hydrocarbons represents an elegant strategy for the one-pot synthesis complex carbonyl compounds. However, this is currently focused on 1,2-difunctionalization olefins or alkynes, and 1,4-alkylcarbonylation 1,3-enynes remains unexplored. In study, we report a Ni-catalyzed CF3-containing under 1 atm CO, which affords tetra-substituted CF3-allenyl ketones with good yields selectivity. This protocol features mild conditions, broad substrate scope, acceptable functional group compatibility. Control experiments revealed that reactivity oxime esters (regulated by leaving groups) polarity matching are crucial success cascade. Preliminary mechanistic studies suggest acyl nickel key intermediate in transformation.
Language: Английский
Citations
26
Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(11), P. 109685 - 109685
Published: March 1, 2024
Language: Английский
Citations
8
Organic Letters, Journal Year: 2024, Volume and Issue: 26(9), P. 1834 - 1839
Published: Feb. 22, 2024
Efficient access to multiple functionalized allenes via a three component 1,4-alkylcyanation of enynes with cyclic alcohol derivatives in the presence trimethylsilyl cyanide (TMSCN) under copper/photoredox dual catalysis has been developed. Both easily transformable aldehyde and cyano groups were introduced tetra-substituted through light-induced C–C bond cleavage butanol pentanol derivatives. The reactions proceeded smoothly mild conditions broad functional tolerance.
Language: Английский
Citations
7
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(12), P. 3485 - 3490
Published: Jan. 1, 2024
Herein, we report electrochemically mediated trifluoromethylallene synthesis via the rearrangement of trifluoromethyl-containing 1,3-enynes under action silicon or boron radicals, with good selectivity and without external oxidants.
Language: Английский
Citations
5
Organic Letters, Journal Year: 2024, Volume and Issue: 26(28), P. 6030 - 6034
Published: July 8, 2024
A photoredox-catalyzed sequential decarboxylative/defluorinative aminoalkylation of CF3-alkenes with N-arylglycines is described. This metal-free and redox-neutral protocol provided efficient access to the monofluoroalkenyl-1,5-diamines in good yields excellent functional group compatibility. Mechanistic studies revealed that reaction proceeds via a radical pathway gem-difluoroalkenyl amine as an intermediate.
Language: Английский
Citations
5
Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(17), P. 2023 - 2028
Published: April 30, 2024
Comprehensive Summary A general and broadly applicable copper photoredox dual‐catalyzed multicomponent 1,4‐perfluoroalkylcyanation of 1,3‐enynes has been developed. This protocol enjoys success with high regioselectivity, mild reaction conditions, excellent functional‐group tolerance, allowing the facile synthesis structurally diverse perfluoroalkylated allenes from readily available fluoroalkyl halides, TMSCN in a one‐pot manner. reasonable mechanism proposed according to series control experiments.
Language: Английский
Citations
4
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: March 24, 2025
The indole skeleton exists widely in natural products, pharmaceuticals, and materials. We disclose here a trifluoromethyl group induced regioselective Larock synthetic method from unsymmetric 2-CF3-1,3-enynes. presence of is determinable for the regioselectivity. Once CF3 was replaced with methyl or phenyl group, ratio 1:1 to 1:1.4 isomers were obtained. This strategy features good regioselectivity, broad substrate scope, high functional tolerance. protocol reported offers an alternative solution rare 3,4-functionalization products further transformed show distinctive reactivity hydroboration–oxidation hydro-bromination.
Language: Английский
Citations
0
Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(2), P. 284 - 289
Published: Oct. 20, 2023
We present a comprehensive account of the regio- and diastereoselective radical multicomponent 1,2-dialkylation 1,3-enynes via photoexcited Hantzsch ester chromium co-catalysis to furnish highly valuable homopropargylic alcohols.
Language: Английский
Citations
5
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10796 - 10804
Published: July 19, 2024
Catalytic difunctionalization with the direct activation of (O)P-H bonds has been recently established as a potentially robust platform to generate valuable organophosphorus compounds. In terms 1,3-enynes, despite various catalytic methods developed for hydrophosphorylation, radical-mediated hetero-functionalization two different atoms less explored. this study, we disclosed an electrochemically induced hydroxyphosphorylation 1,3-enynes construction phosphinyl-substituted propargyl alcohols. The system involves both arylphosphine oxides and oxygen in ambient air no external metal or additive needed. use electrochemistry ensures regioselective, atom-economic eco-friendly process. This strategy highlights advantages mild reaction conditions, readily available starting materials broad substrate scope, showing its practical synthetic value organic synthesis.
Language: Английский
Citations
1
Chemical Science, Journal Year: 2024, Volume and Issue: 15(33), P. 13271 - 13278
Published: Jan. 1, 2024
The radical-mediated difunctionalization of 1,3-enynes facilitates rapid access to structurally diverse allenes and dienes.
Language: Английский
Citations
1