Iodide/Nickel Co-Catalyzed Manganese-Mediated Denitrogenative Cross-Electrophile Coupling of Benzotriazinones with Alkyl Sulfonates DOI Creative Commons

Yingying Hong,

Xuanxuan Zhang,

Gang Zou

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(11), P. 2397 - 2397

Published: May 30, 2025

An efficient Ni-catalyzed, Mn-mediated denitrogenative cross-electrophile coupling of N-alkyl-1,2,3-benzotriazinones with alkyl tosylates and mesylates for access to o-alkyl secondary benzamides is reported. The method uses inexpensive non-anhydrous dimethyl acetamide (DMA) in combination tetrabutyl ammonium iodide (TBAI) as a co-catalyst convert sulfonates into iodides situ. Scope limitations the protocol have been demonstrated by >30 examples yields up 91%, showing large electronic effect from N-substituent benzotriazinones. unexpected steric acceleration has observed core benzotriazinones, not only promising highly 2-alkyl-2,3-disubstituted but also shedding light on rate-limiting steps catalytic cycle.

Language: Английский

Iodide/Nickel Co-Catalyzed Manganese-Mediated Denitrogenative Cross-Electrophile Coupling of Benzotriazinones with Alkyl Sulfonates DOI Creative Commons

Yingying Hong,

Xuanxuan Zhang,

Gang Zou

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(11), P. 2397 - 2397

Published: May 30, 2025

An efficient Ni-catalyzed, Mn-mediated denitrogenative cross-electrophile coupling of N-alkyl-1,2,3-benzotriazinones with alkyl tosylates and mesylates for access to o-alkyl secondary benzamides is reported. The method uses inexpensive non-anhydrous dimethyl acetamide (DMA) in combination tetrabutyl ammonium iodide (TBAI) as a co-catalyst convert sulfonates into iodides situ. Scope limitations the protocol have been demonstrated by >30 examples yields up 91%, showing large electronic effect from N-substituent benzotriazinones. unexpected steric acceleration has observed core benzotriazinones, not only promising highly 2-alkyl-2,3-disubstituted but also shedding light on rate-limiting steps catalytic cycle.

Language: Английский

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