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

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3828 - 3833

Published: April 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.

Language: Английский

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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, Journal Year: 2025, Volume and Issue: unknown

Published: May 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.

Language: Английский

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

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 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

Language: Английский

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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, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 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.

Language: Английский

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

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15901 - 15913

Published: Oct. 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.

Language: Английский

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

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 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.

Language: Английский

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