Silver-Catalyzed Doyle–Kirmse Reaction of Allyl Sulfides with Vinyl Triftosylhydrazones

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 7, 2025

Here, we report a general and practical Doyle-Kirmse reaction of allyl/propargyl sulfides with donor-only vinyl carbenes generated in situ from triftosylhydrazones the presence silver catalyst. This protocol features mild conditions, exhibits broad substrate scope exceptional functional group tolerance, provides corresponding 1,5-dienyl 1,4-enallenyl high yields. Moreover, gram-scale synthesis, late-stage modifications complex molecules, post-synthetic transformations were performed to demonstrate applicability this protocol.

Language: Английский

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Rhodium(II)-Catalyzed Alkynyl Carbene Insertion into N–H Bonds

Organic Letters, Journal Year: 2024, Volume and Issue: 26(23), P. 4887 - 4892

Published: June 6, 2024

The first insertion of an alkynyl carbene into N–H bonds under Rh-catalysis is developed. Alkynyl hydrazone carboxylates are used as donor–acceptor precursors and exquisitely inserted the various amines, amides, 1,2-diamines. A wide variety 3-alkynyl 3,4-dihydroquinoxalin-2(1H)-ones densely functionalized α-alkynyl α-amino esters obtained in good to excellent yields. Further, chemoselective reactions, mechanistic studies, synthetic transformations for obtaining valuable heterocycles demonstrated.

Language: Английский

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On-water synthesis of 3,6-dihydro-2H-thiopyrans: Doyle-Kirmse reaction induced by blue-LED and ring-closing metathesis

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(32), P. 14305 - 14310

Published: Jan. 1, 2024

Water-mediated synthesis of 3,6-dihydro-2 H -thiopyrans from diallyl sulfides and diazo compounds via Doyle–Kirmse reaction induced by blue-LEDs ring-closing metathesis.

Language: Английский

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