Diastereoselective 1,2-difunctionalization of 1,3-enynes enabled by merging photoexcited Hantzsch ester with chromium catalysis

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

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Copper‐Catalyzed Intramolecular Radical Amination of Tertiary C(sp³)−H Bonds to Access α‐Quaternary Pyrrolidines

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(7)

Published: June 3, 2023

Abstract Herein, we describe a Cu(I)/phosphoric acid catalyzed intramolecular radical tertiary C(sp 3 )−H amination of N‐chlorosulfonamide, providing an applicable route to the pyrrolidine structural motifs bearing α‐quaternary stereocenter (>20 examples with up 94 % yield). Mechanistic studies indicate that reaction involves 1,5‐hydrogen atom transfer process form key C‐centered followed by C−N bond formation. The corresponding enantioselective is accordingly disclosed Cu(I)/chiral phosphoric catalyst afford chiral products 81 enantiomeric excess (ee). This strategy anticipated facilitate development functionalization.

Language: Английский

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Electrochemically Enabled Hydroxyphosphorylation of 1,3-Enynes to Access Phosphinyl-Substituted Propargyl Alcohols

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

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Copper-Catalyzed, Intramolecular Amination of Unactivated C(sp³)–H Bonds through Radical Relay

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13077 - 13084

Published: Aug. 29, 2024

Although copper-catalyzed amination of activated C(sp3)–H bonds through radical relay has been developed, unactivated is rare. Herein, intramolecular remote reported. The reaction conducted in a mild and effective manner with moderate to good yields, demonstrating broad tolerance toward various functional groups exhibiting complete regio- chemoselectivities. This innovation supplies novel synthetic pathways for the construction saturated nitrogenated heterocycles.

Language: Английский

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N-Directed, Radical Relay Enantioconvergent Sulfinylation of Distal C(sp³)–H Bonds via Cobalt Catalysis

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 17, 2024

Cobalt-catalyzed enantioconvergent cross-coupling of C(sp

Language: Английский

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Seven-membered rings

Progress in heterocyclic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 569 - 628

Published: Jan. 1, 2023

Language: Английский

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