Photocatalytic Thio/Selenosulfonylation–Bicyclization of Indole-Tethered 1,6-Enynes Leading to Substituted Benzo[c]pyrrolo[1,2,3-lm]carbazoles

Organic Letters, Год журнала: 2024, Номер 26(18), С. 3828 - 3833

Опубликована: Апрель 29, 2024

The photocatalyzed radical-triggered thio/selenosulfonylation–bicyclization of indole-tethered 1,6-enynes has been established for the first time, enabling synthesis various previously unreported thio/selenosulfonylated benzo[c]pyrrolo[1,2,3-lm]carbazoles with moderate to good yields under mild conditions. reaction pathway was proposed, consisting energy transfer, homolytic cleavage, radical addition, 5-exo-dig, coupling, and a Mallory cascade. This approach exhibits wide substrate compatibility excellent tolerability toward functional groups is characterized by its remarkable efficiency in both bond formation annulation.

Язык: Английский

---

A General Electron Donor‐Acceptor Photoactivation Using Oxime Esters Enabled Divergent Thioetherifications^†

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(22), С. 2751 - 2756

Опубликована: Июль 12, 2024

Comprehensive Summary The EDA complex‐mediated reactions involving oxime esters have been few studied. Herein, an complex formed by thiophenolate anion and ester is reported for photoinduced divergent synthesis of thioethers, depending on different types esters. Operational simplicity, mild reaction conditions, flexible options leaving group demonstrate the generality synthetic utility this approach. Such approach can also enable interesting thiol‐catalysis phenanthridines.

Язык: Английский

---

Organophotocatalytic Three‐Component Assembly of C4‐Cyanoalkylated Phthalazin‐1(2H)‐Ones

Chemistry - An Asian Journal, Год журнала: 2025, Номер unknown

Опубликована: Фев. 14, 2025

Abstract The present work documents construction of C4‐cyanoalkylated phthalazinones under visible light‐mediated conditions. three‐component reaction involving aryl hydrazines, 2‐formylbenzoic acids and cyclobutanone oxime esters with organic dye Eosin Y as photocatalyst, features initial formation subsequent cyanoalkylation phthalazin‐1(2H)‐one in one pot. is notable for mild conditions, operational simplicity, wide substrate scope good yields the products. phthalazinone products were further converted into other valuable derivatives.

Язык: Английский

---

Modular reductive radical-polar crossover-based acyl migration reactions of N-vinylimides with alkyl, silyl, and acyl radicals

RSC Advances, Год журнала: 2025, Номер 15(15), С. 11582 - 11586

Опубликована: Янв. 1, 2025

Generation of α-amino ketones: photocatalytic radical addition/acyl migration cascade processes were reported on reactions enamides with dihydroquinazolinones or acyl oxime acetates.

Язык: Английский

---

Construction of C–S and C–Se Bonds via Photocatalytic Aromatization-Driven Deconstructive Diversification of Spiro-Dihydroquinazolinones Derived from Unstrained Ketones

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 13, 2025

A novel and robust deconstructive functionalization reaction of spiro-dihydroquinazolinones with sulfenylating reagents in the presence base has been realized under visible light irradiation. This enabled direct ring-opening unstrained cyclic ring systems, producing skeletally diverse functionalized quinazolinones moderate to good yields. range variety including diaryl disulfide, thiosulfonate, dithiosulfonate 1-[(trifluoromethyl)thio]-2,5-pyrrolidinedione were compatible for this transformation. In addition, diselenide selenosulfonate could also couple form C-Se Bonds. Mechanistic studies revealed that proceeds via a radical-radical coupling pathway.

Язык: Английский

---

Molecular Editing of Cycloketones via Deoxygenative Coupling Enabled by Dual Photoexcited Palladium and Photoredox Catalysis

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 29, 2025

Comprehensive Summary Herein, we report an unprecedented molecular editing strategy for cycloketones that involves the precise translocation and removal of single oxygen atom enabled by dual photoexcited palladium photoredox catalysis. In contrast to conventional ketone strategies, which often rely on loss pre‐functionalized groups or addition additional acylating agents, this approach facilitates efficient recycling moieties. This is accomplished through a catalyzed N–O bond cleavage cycloketone oxime esters, generating cyanoalkyl radicals carboxylate complex. The subsequent photoredox‐catalyzed deoxygenation, mediated phosphoranyl radicals, then leads coupling ultimately yielding desired products. features good economy due skeletal modifications, broad compatibility with various functional groups, significant potential late‐stage functionalization pharmaceutical derivatives.

Язык: Английский

---

Assembly of Functionalized gem-Difluoroalkenes via Photocatalytic Defluorocyanoalkylation and Defluoroacylation of α-CF3 Styrenes with Oxime Esters

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

We report an efficient photocatalytic protocol for the defluorocyanoalkylation and defluoroacylation of α-trifluoromethyl styrenes by utilizing oxime esters as radical donors, allowing preparation diverse

Язык: Английский

---

Visible Light-Promoted and Catalyst-Controlled α-Aminoalkylation and α-Diaminoalkylation of Morita-Baylis–Hillman Acetates with N-Methyl Arylamines: Divergent Synthesis of N-Containing Alkyl Acrylates and γ,γ-Diaminobutyl Esters

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 2, 2024

Visible light-promoted α-aminoalkyl radical-triggered α-aminoalkylation and α-diaminoalkylation of Morita-Baylis–Hillman acetates with N-methyl arylamines to synthesize N-containing alkyl acrylates γ,γ-diaminobutyl esters was reported. Photoinduced is carried out Na2-eosin Y as an organophotocatalyst at room temperature under metal- oxidant-free conditions. In particular, the performed via radical addition/elimination followed by a catalyst-controlled selective addition strategy in one step [Ir(dtbbpy)(bpy)2)]PF6/KF catalytic system. The reaction highly atom- step-economic, high selectivity, furnishing butyl moderate good yields wide substrate scope.

Язык: Английский

---

Photoredox-Catalyzed Alkynylation of C(sp³)-H Bonds Adjacent to a Nitrogen Atom of Tertiary Amines with Alkynyl Bromides

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(21), С. 15901 - 15913

Опубликована: Окт. 12, 2024

A novel and robust alkynylation of C(sp3)–H bonds adjacent to a nitrogen atom tertiary amines with alkynyl bromides as radical alkynylating reagents has been realized under visible-light irradiation. range variety including N-arylamines N-alkylamine have coupled both aromatic aliphatic furnish 51 examples propargylamines in moderate excellent yields (31–80% yields). The possible mechanism was addition–elimination process based on preliminary mechanistic studies.

Язык: Английский

---

Photo‐catalyzed Stereospecific Synthesis of Trisubstituted Alkenes Incorporating 3,3‐Difluoro‐γ‐Lactams from Morita‐Baylis‐Hillman Acetates and N‐Allylbromodifluoroacetamides

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 1, 2024

Abstract A photocatalytic methodology has been devised for the stereoselective construction of trisubstituted alkenes incorporating 3,3‐difluoro‐γ‐lactams in 17–93% yields via a radical cascade process utilizing MBH acetates and N ‐allylbromodifluoroacetamides as starting materials. The reaction mechanism involves single‐electron transfer, 5 ‐ exo trig cyclization, addition, elimination fashion.

Язык: Английский

---