Regioselective, Lewis Acid-Catalyzed Ring-Openings of 2,3-Aziridyl Alcohols with Azoles

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 25, 2025

Methods for regioselective ring-opening reactions of N-sulfonyl-protected aziridyl alcohols with azole nucleophiles have been developed. Several classes azoles, including indazole, substituted pyrazole, benzotriazole, and tetrazole, employed as reaction partners, giving rise to C3-selective opening >3:1 N-selectivity. BF3•OEt2 is the optimal catalyst most substrate combinations, although examples where diphenylborinic acid (Ph2BOH) provides higher yields, or proceed efficiently without a catalyst, are also described. Computational modeling BF3•OEt2-catalyzed consistent observed regiochemical outcome. The calculated transition state appears be stabilized by an unconventional OH···FB hydrogen-bonding interaction.

Язык: Английский

Facile Generation of Trideuteromethyl Radical from Alkylsilyl Peroxide and Subsequent Functionalization

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(11)

Опубликована: Авг. 23, 2024

Abstract Cu‐ and Fe‐ catalyzed trideuteromethylation reactions using alkylsilyl peroxide as trideuteromethyl radical precursor are reported. The was synthesized from acetone‐d6 in a three‐step sequence, the with various coupling partners afforded efficiently corresponding N−CD 3 , O−CD C−CD bond formation products. heptadeuteriopropylation prepared butyric acid‐d7 is also described.

Язык: Английский