光氧化还原/钴协同催化炔烃、N-甲基胺和水的羟甲基化反应

doi:10.1016/S1872-2067(26)65076-0

催化学报 ›› 2026, Vol. 87: 197-205.DOI: 10.1016/S1872-2067(26)65076-0

光氧化还原/钴协同催化炔烃、N-甲基胺和水的羟甲基化反应

李彦霖^a^,^*(), 郭宁欣^b^,^c, 毕佳婷^a, 薛凌雨^a, 朱月路^a, 邵友东^a^,^*(), 夏纪宝^b^,^c^,^*()

^a 菏泽学院化学化工学院, 山东菏泽 274015
^b 中国科学院兰州化学物理研究所, 低碳催化与二氧化碳利用国家重点实验室, 甘肃兰州 730000
^c 中国科学院大学, 北京 100049

收稿日期:2025-11-27 接受日期:2026-01-15 出版日期:2026-08-18 发布日期:2026-06-24
通讯作者: ^*电子信箱: liyanlinhzu@163.com (李彦霖),
shaoyd2015@163.com (邵友东),
jibaoxia@licp.cas.cn (夏纪宝).
基金资助:
山东省自然科学基金(ZR2024QB016);菏泽学院博士基金(XY23BS21);国家自然科学基金(22271296);国家自然科学基金(22471279)

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

Yan-Lin Li^a^,^*(), Ning-Xin Guo^b^,^c, Jia-Ting Bi^a, Ling-Yu Xue^a, Yue-Lu Zhu^a, You-Dong Shao^a^,^*(), Ji-Bao Xia^b^,^c^,^*()

^a School of Chemistry and Chemical Engineering, Heze University, Heze 274015, Shandong, China
^b State Key Laboratory of Low Carbon Catalysis and Carbon Dioxide Utilizations, Suzhou Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, Gansu, China
^c University of Chinese Academy of Sciences, Beijing 100049, China

Received:2025-11-27 Accepted:2026-01-15 Online:2026-08-18 Published:2026-06-24
Supported by:
Shandong Provincial Natural Science Foundation(ZR2024QB016);Heze University Scientific Research Foundation(XY23BS21);National Natural Science Foundation of China(22271296);National Natural Science Foundation of China(22471279)

摘要/Abstract

摘要：

利用单一水分子同时提供氢与氧原子以构建高附加值产物, 是实现原子经济和绿色合成的理想路径之一, 然而该类策略在有机合成中的应用仍极为有限. 三取代烯丙醇是重要的合成中间体, 直接高效的合成方法包括炔烃与外源性含氧碳一试剂(甲醛、二氧化碳或甲醇)的直接还原羟甲基化.而以水作为氧源构建此类化合物的方法尚未见报道.在可见光催化反应中, 三级胺常作为电子给体、氢源或底物参与反应. 与产生高分子量副产物(多取代吡啶衍生物)的Hantzsch酯相比, 三级胺作还原剂时转化生成的副产物分子量低, 故而更具合成优势. 然而, 水与N-烷基胺同时作为反应组分, 与其他分子偶联合成含氧化合物的策略, 至今仍未实现. 因此, 开发一种以三级胺和水作为原料构建烯丙醇的催化体系, 将为实现光催化羟甲基化反应提供更理想和高效的催化模式.

本文通过高效的可见光光致氧化还原/钴协同催化策略, 使用易得的炔烃、N-甲基二异丙基胺(ⁱPr₂NMe)和H₂O为原料, 在温和条件下高效实现了炔烃的羟甲基化反应. 该反应成功的关键在于, 将光致氧化还原催化与钴催化相结合, 利用N-甲基胺作为碳一合成子和电子给体, 以H₂O作为绿色的氢源与氧源, 避免使用传统外源性甲醛或其他含氧C1试剂. 反应以2,4,5,6-四(9-咔唑基)-间苯二腈(4CzIPN)作为光敏剂, 三环己基膦(PCy₃)为配体, H₂O作为氢源和氧源, ⁱPr₂NMe作为碳一合成子和电子给体, 乙腈作为溶剂, 实现了三取代烯丙醇的合成. 结果表明, 该方法对炔烃底物具有良好的适用性, 包括烷基、烯基、酯基、羟基、胺基、环丙基和离去基团(OTs)等非对称的芳基烷基内炔, 均能与H₂O和ⁱPr₂NMe有效偶联, 并以较高收率得到目标产物. 同时, 芳基上带有各种富电子和缺电子基团的炔烃也能较好地参与反应. 值得关注的是, 该方法成功应用于多种生物活性分子(如雌酮、薄荷醇、非诺贝特酸)骨架的炔烃衍生物的后期修饰, 并可用于癌症化疗药物Epothilone B关键中间体的合成, 充分展示了其在药物化学及功能分子合成中的潜在应用价值. 对胺结构的考察表明, 胺的位阻对该反应有着显著影响, 大位阻取代基的甲基胺作为底物时, 反应能够较好的进行. 通过系统的氘代实验和控制实验, 揭示了该反应机制. 反应经过光钴协同催化的N-甲基胺与水的选择性C‒N键断裂生成甲醛, 随后其与炔烃生成五元环钴中间体, 经质子化和单电子还原后得到目标产物.

综上, 本文发展了一种钴催化炔烃的选择性羟甲基化新方法. 通过可见光/钴协同催化策略, 以H₂O和N-甲基胺作为羟甲基源, 在温和的条件下实现了具有优异区域选择性和立体选择性的三取代烯丙醇的合成. 本文为炔烃的羟甲基化反应提供了一种绿色、简单、高效的新途径, 为三级胺在合成化学中的高值化利用提供了新思路.

关键词: 羟甲基化反应, 水, N-甲基胺, 光钴协同催化, 炔烃

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.

Key words: Hydroxymethylation, Water, Methylamine, Photoredox cobalt dual catalysis, Alkyne

李彦霖, 郭宁欣, 毕佳婷, 薛凌雨, 朱月路, 邵友东, 夏纪宝. 光氧化还原/钴协同催化炔烃、N-甲基胺和水的羟甲基化反应[J]. 催化学报, 2026, 87: 197-205.

Yan-Lin Li, Ning-Xin Guo, Jia-Ting Bi, Ling-Yu Xue, Yue-Lu Zhu, You-Dong Shao, Ji-Bao Xia. Hydroxymethylation of alkynes with N-methylamines and water enabled by Co/photoredox dual catalysis[J]. Chinese Journal of Catalysis, 2026, 87: 197-205.

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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(26)65076-0

https://www.cjcatal.com/CN/Y2026/V87/I8/197

图/表 7

Fig. 1. Selective coupling of N-methyl amines via photoredox metal dual catalysis.

Fig. 2. Initial result for the unusual hydroxymethylation. Reaction conditions: 1 (0.2 mmol), 2 (0.4 mmol), H2O (5.0 eq.), 4CzIPN (2 mol%), CoCl2 (10 mol%), Xantphos (10 mol%), MeCN (2 mL), 5 W blue LED, r.t., 24 h; Yield, rr, E/Z were determined by crude 1H NMR with 1,1,2,2 tetrachloroethane as an internal standard.

Table 1 Summary of the effects of reaction parameters on the reaction efficiency a.

Entry	Change from “standard conditions”	Yield (%)	rr	E/Z
1	none	81 (78)^b	>19:1	>19:1
2	PPh₃ instead of PCy₃	70	>19:1	>19:1
3	NiXantphos instead of PCy₃	61	13:1	>19:1
4	DPEphos instead of PCy₃	67	3.3:1	>19:1
5	DPPF instead of PCy₃	37	4:1	>19:1
6	DPPE instead of PCy₃	41	6:1	>19:1
7	DPPP instead of PCy₃	36	4:1	>19:1
8	DCyPE instead of PCy₃	20	12:1	>19:1
9	DMF instead of MeCN	45	>19:1	>19:1
10	MeOH instead of MeCN	21	>19:1	>19:1
11	2c (4 eq.)	79	>19:1	>19:1
12	H₂O (10 eq.)	80	>19:1	>19:1
13	without 2c	N.R.	—	—
14	without H₂O	N.R.	—	—

Fig. 3. Reaction scope. Reaction conditions: alkyne (0.2 mmol), 2c (0.4 mmol), H2O (5.0 eq.), 4CzIPN (2 mol%), CoCl2 (10 mol%), PCy3 (20 mol%), MeCN (2 mL), 5 W blue LED, r.t., 24 h. if otherwise noted. Isolated yield of product is provided. The regioselectivity (rr) for alkyne and the stereoselectivity (E/Z) of the product were determined by crude 1H NMR. a The reaction was performed with 8.0 mmol alkyne 1 as the substrate. b With DCyPE as ligand.

Fig. 4. Transformation and application of the products. Reagents and conditions: (A) m-CPBA, DCM, r.t., 75%; (B) Chloramine-T, NBS (20 mol%), MeCN, r.t., 71%; (C) SOCl2, DCM, 0 °C, 79%; (D) RuCl3 (10 mo%), NaIO4, MeCN/CCl4/H2O, r.t., 49%; (E) PPh3, phthalimide, DIAD, THF, 0 °C r.t., 41%; (F) PPh3, DIAD, THF, 0 °C r.t., 61%.

Fig. 5. Control experiments.

Fig. 6. Plausible reaction pathway.

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光氧化还原/钴协同催化炔烃、N-甲基胺和水的羟甲基化反应

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

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