Photochemical C3-amination of pyridines via Zincke imine intermediates

Nature Communications, Год журнала: 2025, Номер 16(1)

Опубликована: Май 31, 2025

Язык: Английский

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The Construction of Highly Substituted Piperidines via Dearomative Functionalization Reaction

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(49)

Опубликована: Окт. 20, 2023

Nitrogen heterocycles play a vital role in pharmaceuticals and natural products, with the six-membered aromatic aliphatic architectures being commonly used. While synthetic methods for N-heterocycles are well-established, synthesis of their functionalized analogues, particularly piperidine derivatives, poses significant challenge. In that regard, we propose stepwise dearomative functionalization reaction construction highly decorated derivatives diverse functional handles. We also discuss challenges related to site-selectivity, regio- diastereoselectivity, provide insights into mechanism through mechanistic studies density theory computations.

Язык: Английский

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Direct C3‐H Alkylation and Alkenylation of Quinolines with Enones

Angewandte Chemie International Edition, Год журнала: 2024, Номер 64(1)

Опубликована: Сен. 19, 2024

Conversion of quinoline C-H bonds into C-C is essential for obtaining the enormous array derivatives required pharmaceutical and agrochemical development. Despite over a century synthetic efforts, direct alkylation alkenylation at C3-H positions in wide precursors remain predominantly challenging elusive. This report outlines first successful reactions, exhibiting exceptional regio- stereoselectivity, all achieved under redox-neutral transition-metal-free conditions. The method involves three-step, one-pot or two-pot sequence, including 1,4-dearomative addition, functionalization C3, elimination transalkylation to produce 3-alkylated/alkenylated quinolines. presence carbonyl group these products allows further manipulations, enabling production cyanides, amides, amines, simple alkyl derivatives.

Язык: Английский

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Tributyl(1-((dimethylamino)(dimethyliminio)methyl)-1,4-dihydropyridin-4-yl)phosphonium Ditrifluoromethanesulfonate

Molbank, Год журнала: 2023, Номер 2023(3), С. M1710 - M1710

Опубликована: Авг. 9, 2023

Site-selective functionalization of pyridines is a crucial tool for the synthesis diverse pharmaceuticals and materials. We introduced diiminium pyridine adducts as highly convenient potent Lewis acids. report that tributylphosphine selectively adds to 4-position in tetramethyldiiminium ditrifluoromethanesulfonate, resulting formation title compound. This finding represents an advancement towards utilization units organic reagents or catalysts functionalization. also employ computational models determine fluoride hydride ion affinities, Fukui function f+(r), molecular electrostatic potential, pKa values, providing valuable insights future investigations this area.

Язык: Английский

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Rhodium-Catalyzed Asymmetric Functionalization of Quinoxalinium Salts

Organic Letters, Год журнала: 2023, Номер 25(50), С. 8987 - 8991

Опубликована: Дек. 7, 2023

We report a rhodium-catalyzed asymmetric addition of aryl and alkenyl boronic acids to quinoxalinium salts that generates dihydroquinoxalines with high enantioselectivity. Functionalization the reaction products, dihydroquinoxaline, allows preparation tetrahydroquinoxalines various substitution patterns.

Язык: Английский

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