Hydroxymethylation of alkynes with N-methylamines and water enabled by Co/photoredox dual catalysis

IF 17.2 1区化学 Q1 CHEMISTRY, APPLIED

Chinese Journal of Catalysis Pub Date : 2026-08-01 Epub Date: 2026-08-02 DOI:10.1016/S1872-2067(26)65076-0

Yan-Lin Li, Ning-Xin Guo, Jia-Ting Bi, Ling-Yu Xue, Yue-Lu Zhu, You-Dong Shao, Ji-Bao Xia

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Abstract

Water is an ideal hydrogen or oxygen source in chemical synthesis. However, many organic reactions are unable to utilize this potential or even incompatible with aqueous conditions. Here, we report a synergistic visible light organophotoredox Co-catalyzed highly regio- and stereoselective hydroxymethylation of alkynes with N-methylamines and water. This method employs water as both hydrogen (H) and oxygen (O) donor, with N-methyl trialkylamines serving as C1 synthon and photoredox reductant, thereby eliminating exogenous oxygenated C1 reagents. A variety of tri-substituted allylic alcohols have been obtained with excellent regio- (up to >19:1 rr) and stereoselectivity (> 19:1 E/Z for over 30 examples). Mechanistic studies reveal two critical water assistant processes involving selective C–N cleavage of N-methylamines generating formaldehyde and subsequent regioselective reductive hydroxymethylation of alkynes via photoredox cobalt dual catalysis.

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Co/光氧化还原双催化使炔与n -甲胺和水发生羟甲基化

水是化学合成中理想的氢或氧源。然而，许多有机反应不能利用这种潜力，甚至与水条件不相容。在这里，我们报道了一个协同可见光有机光氧化还原协同催化的高度区域和立体选择性羟甲基化的炔与n -甲胺和水。该方法以水作为氢(H)和氧(O)的供体，以n -甲基三烷基胺作为C1合子和光氧化还原还原剂，从而消除了外源性的含氧C1试剂。得到了多种三取代烯丙基醇，具有优异的区域选择性（高达>；19:1 rr）和立体选择性（> 19:1 E/Z，有30多个例子）。机理研究揭示了两个关键的水辅助过程，包括n -甲胺的选择性C-N裂解生成甲醛和随后通过光氧化还原钴双催化的炔的区域选择性还原羟甲基化。

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来源期刊

Chinese Journal of Catalysis 工程技术-工程：化工

CiteScore

25.80

自引率

10.30%

发文量

235

审稿时长

1.2 months

期刊介绍： The journal covers a broad scope, encompassing new trends in catalysis for applications in energy production, environmental protection, and the preparation of materials, petroleum chemicals, and fine chemicals. It explores the scientific foundation for preparing and activating catalysts of commercial interest, emphasizing representative models.The focus includes spectroscopic methods for structural characterization, especially in situ techniques, as well as new theoretical methods with practical impact in catalysis and catalytic reactions.The journal delves into the relationship between homogeneous and heterogeneous catalysis and includes theoretical studies on the structure and reactivity of catalysts.Additionally, contributions on photocatalysis, biocatalysis, surface science, and catalysis-related chemical kinetics are welcomed.