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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Photocatalytic Bicyclization of Indole-Tethered 1,6-Enynes for Diastereoselective Synthesis of Pyrrolo[3,2,1-jk]carbazoles

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3810 - 3815

Published: April 28, 2024

A visible-light-driven photocatalytic protocol is established for the diastereoselective synthesis of pyrrolo[3,2,1-jk]carbazoles via a radical-triggered multicomponent bicyclization reaction starting from readily available indole-tethered 1,6-enynes and α-benzyl-α-bromomalonates under mild conditions. This approach exhibits wide substrate compatibility excellent tolerability toward various functional groups boasts benefit efficient ring formation chemical bond creation.

Language: Английский

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Copper‐catalyzed radical‐induced annulation‐halo(bi)cyanomethylation of indole‐tethered 1,6‐enynes toward pyrrolo[1,2‐a]indoles

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(17), P. 3578 - 3584

Published: June 18, 2024

Abstract A copper‐catalyzed radical‐induced annulation‐halocyanomethylation of indole‐linked 1,6‐enynes has been established using haloacetonitrile as radical precursors, enabling the synthesis 21 cyanomethylated pyrrolo[1,2‐ a ]indoles with yields ranging from 42% to 81% and Z / E ratio up 19:1. Moreover, by adjusting reaction temperature, variation annulation‐bromobicyanomethylation process was achieved, resulting in production 12 bicyanomethylated ]indole isomers 41–68%. The stereoisomeric mixture products could be purified their pure configurations through recrystallization. proposed mechanism formulated series control experiments.

Language: Английский

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Accessing pyrrolo[1,2-a]indole derivatives via visible-light-induced dearomatizative cyclization of indoles

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(37), P. 4902 - 4905

Published: Jan. 1, 2024

Dearomatizative cyclization of indoles: a novel synthetic method for pyrrolo[1,2- ]indole derivatives through visible-light-induced cascade dearomatizative indoles with external nucleophiles has been developed.

Language: Английский

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Photocatalyzed Annulation‐Biselenylation of Enynone with Diarylselenides toward Biselenium‐Substituted 1‐Indanones under Metal‐ and Photosensitizer‐Free Conditions

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 17, 2025

Comprehensive Summary A practical photocatalytic annulation‐biselenylation strategy has been developed for the efficient synthesis of biselenium‐substituted 1‐indanones (38 examples in total) with generally good yields (up to 95%) and excellent stereoselectivity (>19 : 1 Z / E ratio) by employing enynones diaryl selenides as starting materials under photosensitizer‐free conditions. The reaction mechanism involves a cascade process comprising homolytic cleavage, radical addition, 5‐ exo ‐ dig cyclization, capture, enabling sequential formation multiple bonds, such C(sp 3 )‐Se, )‐C(sp 2 ), )‐Se rapidly construct molecular complexity. Notably, this approach demonstrates wide substrate compatibility tolerability towards various functional groups. It is further characterized its remarkable efficiency creating chemical bonds achieving high atomic utilization 100%.

Language: Английский

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Reactions of alkynes with C–S bond formation: recent developments

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(32), P. 6443 - 6484

Published: Jan. 1, 2024

Alkynes are important in organic synthesis. This review mainly focuses on the recent advances (2013–2023) alkynes with C–S bond formation, based more than 30 kinds of sulfur reagents.

Language: Английский

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Assembly of Thiazino[3,4‐a]isoquinoline and Thiazepino[5,4‐a]isoquinoline Frameworks from Isoquinolinium 1,4‐Zwitterionic Thiolates via [5 + 1] and [5 + 2] Cycloaddition Reactions

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

Published: Oct. 18, 2024

Abstract Two cycloaddition modes of isoquinolinium 1,4‐zwitterionic thiolates have been established. Upon choosing α ‐bromo ketones as the counterpart, a range isoquinoline‐fused thiazines can be attained with yields ranging from moderate to excellent through formal [5+1] reaction pathway, exhibiting remarkable substrate adaptability and resilience diverse functional groups. Additionally, library unprecedented thiazepino[5,4‐ ]isoquinolines, novel category seven‐membered heterocycles, has synthesized via [5+2] pathway utilizing acetylenedicarboxylate reactive component. Notably, this process stands out for its exceptional 100 % atomic utilization efficiency.

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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