Synfacts, Journal Year: 2023, Volume and Issue: 19(10), P. 0980 - 0980
Published: Sept. 14, 2023
Key words [3+3] cycloaddition - tetrasubstituted phenols sulfoxonium ylides cyclopropenones
Language: Английский
Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 1, 2025
A novel visible-light-induced photoredox three-component aerobic coupling reaction of sulfoxonium ylides and amines is reported.
Language: Английский
Citations
1
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: March 3, 2025
A novel and efficient method for the synthesis of multisubstituted arylnitriles via Tf2O-mediated [3 + 2 1] benzannulation enaminones acylacetonitriles has been developed. This reaction proceeds under mild conditions with excellent functional group compatibility. Mechanistic studies have revealed that cyclization involves two consecutive nucleophilic additions, followed by a cascade Knoevenagel condensation aromatization. Additionally, trifluoromethanesulfonate 6 identified as crucial intermediate in this process.
Language: Английский
Citations
1
Chemical Communications, Journal Year: 2023, Volume and Issue: 59(83), P. 12411 - 12422
Published: Jan. 1, 2023
Sulfoxonium ylides are important synthetic precursors in various organic transformations. Their potential was well explored the synthesis of bioactive natural products and pharmaceuticals. Vinyl sulfoxonium ylide is a stabilized containing an electron-deficient alkene at ylidic carbon. Similar to α-keto ylides, these reagents can generate vinyl carbenes presence metals under suitable conditions. These be used for transformations such as X-H (X = C, N, O, S) insertions, annulations, rearrangement reactions. Due dipole structure ylide, it undergo electrophilic addition with electrophiles α-position. synthons aromatic heteroaromatic compound syntheses. Moreover, their stability convenient handling make them replacements thermally less stable diazo compounds. Herein, we provide overview early efforts this area, particular emphasis on our own recent development ylide-mediated absence metal catalysis, also give personal perspectives challenges future scope improving application ylides.
Language: Английский
Citations
19
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(11), P. 3234 - 3241
Published: Jan. 1, 2024
Herein, we present a cascade O–H double insertion reaction between I (III) /S (VI) -ylides, carboxylic acids, and alcohols under metal-free conditions, enabling the modular synthesis of unsymmetrical α,α- O , -substituted ketones.
Language: Английский
Citations
8
Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5811 - 5816
Published: June 28, 2024
A practical strategy for the construction of diverse phosphonyl and thiofunctionalized sulfoxonium ylides via controllable monofunctionalization hybrid I(III)/S(VI) is presented. This process allows efficient P–H insertion under Cu catalysis, enabling synthesis ylides, whereas reaction with sulfur-containing reagents including AgSCF3, KSC(S)OR, KSCN mild conditions resulted in α-trifluoromethylthiolation, dithiocarbanation, thiocyanation accordingly. Of note, wide substrate compatibility (108 examples), excellent efficiency (up to 99% yield), gram-scale experiments, various product derivatizations highlight synthetic utility this protocol.
Language: Английский
Citations
7
Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6736 - 6741
Published: July 29, 2024
A visible-light-induced photoredox three-component carbocyclization reaction of 1,7-enynes with sulfoxonium ylides and water is reported. The protocol provides a facile entry to structurally valuable highly functionalized cyclopenta[c]quinoline scaffolds in chemoselective stereoselective manner. Salient features this method include redox-neutral conditions, no requirement base or other additive, good functional-group tolerance.
Language: Английский
Citations
7
Organic Letters, Journal Year: 2023, Volume and Issue: 25(50), P. 8992 - 8996
Published: Dec. 12, 2023
Herein, we report the divergent benzannulation for highly substituted arenes using vinyl sulfoxonium ylides and ynones. The addition of ynone at γ-position leads to dienyl ylide that can undergo selective annulation under different conditions give m-terphenyls parabens. Moreover, control experiments quantum chemical calculations reveal two distinct reaction mechanisms both annulations.
Language: Английский
Citations
11
Arabian Journal of Chemistry, Journal Year: 2024, Volume and Issue: 17(8), P. 105845 - 105845
Published: May 23, 2024
Cyclopropenone has emerged as a highly versatile precursor in organic synthesis due to its diverse reactivity. The cyclopropenone derivatives could undergo various transformations such cycloaddition reactions, ring-opening and isomerization reactions the presence of different chemical reagents. Over years, significant progress been made manipulation cyclopropenones for construction carbocycles, heterocycles, other useful compounds. Despite several reviews that have concerned chemistry cyclopropenones, utility motifs carbocycles heterocycles rarely reported. Herein, we report recent advancements synthetic precursors towards compounds with biological significance.
Language: Английский
Citations
4
Organic Letters, Journal Year: 2023, Volume and Issue: 25(43), P. 7906 - 7910
Published: Oct. 24, 2023
Herein, we report the synthesis of π-conjugation-extended vinyl sulfoxonium ylides from ylide and electron-deficient alkynes. The new dienoate are used in various transformations, such as X-H (X = S, O) insertion, halogenation, carbene-mediated transformation, radical-mediated reductions to obtain a variety conjugated dienoates.
Language: Английский
Citations
9
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown
Published: Jan. 1, 2024
A metal-free protocol for the modular synthesis of diverse α-thiofunctionalized-α′-carbonyl sulfoxonium ylides from sulfoxonium–iodonium hybrid (I (III) /S (VI) -ylides) has been achieved.
Language: Английский
Citations
3