Base-Promoted Regioselective Annulation of Pyridinium Ylides and Bromoalkynes for the Chemodivergent Synthesis of Indolizines

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 5, 2025

A base-promoted regioselective formal [3 + 2] annulation of pyridinium ylides with bromoalkynes is reported, producing a series substituent-diverse indolizines in generally good yields. mild K2CO3-promoted three-component cyclization and at 2:1 molar ratio delivered C2-acylmethylated indolizines, whereas C2-brominated were generated starting from bearing strong electron-withdrawing groups the unit by using 2,2,6,6-tetramethyl-1-piperidinyloxy as dehydrogenating reagent. The current synthetic methodology offers controllable modular approach to access different substitution patterns, featuring wide substrate scope, functional group compatibility, complete regioselectivity without demand any transition-metal catalysts.

Language: Английский

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Photocatalyzed Azidofunctionalization of Alkenes via Radical‐Polar Crossover

Angewandte Chemie International Edition, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 2, 2025

The azidofunctionalization of alkenes under mild conditions using commercially available starting materials and easily accessible reagents is reported based on a radical-polar crossover strategy. A broad range alkenes, including vinyl arenes, enamides, enol ethers, sulfides, dehydroamino esters, were regioselectively functionalized with an azide nucleophiles such as azoles, carboxylic acids, alcohols, phosphoric oximes, phenols. method led to more efficient synthesis 1,2-azidofunctionalized pharmaceutical intermediates when compared previous approaches, resulting in both reduction step count increase overall yield. scope limitations these transformations further investigated through standard unbiased selection 15 substrate combinations out 1,175,658 possible clustering technique.

Language: Английский

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Photocatalyzed Azidofunctionalization of Alkenes via Radical‐Polar Crossover

Angewandte Chemie, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 2, 2025

Abstract The azidofunctionalization of alkenes under mild conditions using commercially available starting materials and easily accessible reagents is reported based on a radical‐polar crossover strategy. A broad range alkenes, including vinyl arenes, enamides, enol ethers, sulfides, dehydroamino esters, were regioselectively functionalized with an azide nucleophiles such as azoles, carboxylic acids, alcohols, phosphoric oximes, phenols. method led to more efficient synthesis 1,2‐azidofunctionalized pharmaceutical intermediates when compared previous approaches, resulting in both reduction step count increase overall yield. scope limitations these transformations further investigated through standard unbiased selection 15 substrate combinations out 1,175,658 possible clustering technique.

Language: Английский

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Access to Functionalized Amines and Medium N-Heterocycles via Amine-Enabled Remote C–H Alkynylation

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

Published: Nov. 14, 2024

By using weakly coordinating amines, we developed remote C-H alkynylation with precise control of reactivity and regioselectivity, enabling modification complex drugs, natural products, materials. The readily transformable alkyne-containing amine products would facilitate expedient delivery molecular libraries functionalized amines medium

Language: Английский

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Palladium-catalyzed syn-alkynylarylation of internal alkynes: rapid access to all-carbon tetrasubstituted alkenes

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(71), P. 9578 - 9581

Published: Jan. 1, 2024

A novel palladium-catalyzed syn -alkynylarylation of internal alkynes with haloalkynes and arylboronic acids is described.

Language: Английский

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