光催化环氧化合物的区域选择性开环反应

doi:10.1016/S1872-2067(26)65016-4

催化学报 ›› 2026, Vol. 85: 34-46.DOI: 10.1016/S1872-2067(26)65016-4

光催化环氧化合物的区域选择性开环反应

李婧宇^a, 徐艺军^a^,^b()

^a 福州大学化学学院, 能源与环境光催化国家重点实验室, 福建福州 350116
^b 电子科技大学, 基础与前沿研究院, 四川成都 611731

收稿日期:2025-09-18 接受日期:2025-11-28 出版日期:2026-06-18 发布日期:2026-05-18
通讯作者: *电子信箱: yjxu@uestc.edu.cn (徐艺军).
基金资助:
国家自然科学基金(22472032);国家自然科学基金(22072023);国家自然科学基金(22172030);国家自然科学基金(21872029);中国电子科技大学杰出人才科研基金(A1098531023601522);国家科技领军人才计划(00387072);江西省“双千计划” (jxsq2023102143);中国留学基金委员会(202306650033)

Regioselective ring-opening of epoxides triggered by light

Jing-Yu Li^a, Yi-Jun Xu^a^,^b()

^a College of Chemistry, State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou University, Fuzhou 350116, Fujian, China
^b Institute of Fundamental and Frontier Sciences, University of Electronic Science and Technology of China, Chengdu 611731, Sichuan, China

Received:2025-09-18 Accepted:2025-11-28 Online:2026-06-18 Published:2026-05-18
Contact: *E-mail: yjxu@uestc.edu.cn (Y.-J. Xu).
Supported by:
National Natural Science Foundation of China(22472032);National Natural Science Foundation of China(22072023);National Natural Science Foundation of China(22172030);National Natural Science Foundation of China(21872029);Research Fund for Outstanding Talents at University of Electronic Science and Technology of China(A1098531023601522);Program for National Science and Technology Innovation Leading Talents(00387072);Jiangxi Province “Double Thousand Plan”(jxsq2023102143);China Scholarship Council(202306650033)

摘要/Abstract

摘要：

环氧化合物因其固有的三元环结构带来的高环张力和极化的C-O键, 在有机合成中被广泛用作构筑醇、羧酸、烯烃等多种官能化产物的关键合成前体, 因此在药物分子、精细化学品以及功能材料合成中具有重要地位. 经典的环氧化物开环策略多依赖于反应条件调节, 实现对环氧环C-O键的选择性活化. 然而, 在底物结构日益复杂、对选择性和绿色性要求不断提高的背景下, 仅依靠传统方式已难以全面满足反应条件温和化、区域选择性可控化及过程可持续化的多重需求. 近年来, 光催化作为一种可持续的新型技术, 能够利用清洁的太阳能激发催化反应体系, 促使环氧化合物C-O键的精准活化与断裂, 为其在温和条件下实现区域选择性开环提供了新的途径.

本综述系统梳理了近年来光催化环氧化合物区域选择性开环反应领域的研究进展. 首先, 简要概述了环氧化合物在酸性和碱性条件下开环位点的差异, 并比较了其在均相光催化与多相光催化两类体系下C-O键断裂的基本作用机制. 随后, 以具体反应类型为主线, 总结了醇解、脱氧、氢解、羧基化、烯丙基化和芳基化等代表性光催化环氧开环反应, 分别归纳了各类反应中关键中间体的形成途径、C-O键断裂方式以及与环氧底物结构和亲核试剂种类之间的关系. 在此基础上, 重点分析了区域选择性调控的核心因素, 包括金属活性中心的电子结构与配位环境、不同金属对氧原子的亲和能力和键能差异, 配体对金属中心电子密度与空间构型的精细调节作用, 亲核试剂的种类及其活化模式, 以及环氧取代基的电子效应和空间位阻对过渡态与中间体稳定性的综合影响, 提出了通过金属位点设计、配体修饰和亲核试剂选择以实现区域选择性调控的思路. 最后, 为深化该领域发展并应对当前挑战, 提出了未来研究需着力于以下紧密关联的方向: 一方面, 目前光催化环氧化物开环在活性表征方面仍缺乏统一的量化标准, 亟需建立兼顾活性、选择性和绿色指标的综合评价体系, 并规范光源和反应器等关键信息的记录与共享. 另一方面, 有必要进一步依托各类原位和工况表征技术, 对短寿命自由基、中间体及催化剂表面状态进行直接观测与动态追踪, 以进一步完善C-O键活化机理. 同时, 随着多通道光反应器、自动化操作平台与智能算法的发展, 将光催化环氧化物开环引入机器人和人工智能辅助的高通量筛选框架, 有望显著加快催化剂与反应条件的优化进程, 并为构建系统化数据库提供基础. 最后, 缺乏明显电子导向效应的脂肪族环氧化合物和内位环氧化合物等底物的高效活化, 以及区域选择性与对映选择性的协同调控, 仍是该领域面临的重要挑战, 需通过催化体系精细设计进一步拓展高效转化的底物适用范围. 希望本文能够为推动光催化环氧化合物开环技术向高效率和精准选择性方向发展提供借鉴.

关键词: 开环反应, 环氧化合物, 光催化, 区域选择性, 绿色化学

Abstract:

Epoxides boast intrinsic ring strain and high reactivity towards various nucleophiles, thus rendering them fundamental building blocks in organic synthesis. Notably, the ring-opening of these readily available compounds offers a versatile strategy to produce a diverse array of valuable functionalized molecules, such as alcohols, carboxylic acids, olefins, etc. However, the conventional reaction systems for ring-opening typically rely on harmful agents or harsh conditions, which limit their applicability in complex molecule synthesis. Recent advancements in photocatalysis have emerged as a sustainable and promising alternative for precise cleavage of strained C−O bonds in epoxides under mild conditions, showcasing rapid development over the past decade. This mini-review examines the mechanisms and strategies for regioselective epoxide ring-opening triggered by varieties of nucleophiles based on photocatalysis, encompassing fundamental concepts of ring-opening, key factors influencing product regioselectivity and the potential impact of operando techniques and artificial intelligence on this field. The persistent challenges and potential trajectory in this dynamic domain are also critically discussed to foster further innovation.

Key words: Ring-opening, Epoxide, Photocatalysis, Regioselectivity, Green chemistry

李婧宇, 徐艺军. 光催化环氧化合物的区域选择性开环反应[J]. 催化学报, 2026, 85: 34-46.

Jing-Yu Li, Yi-Jun Xu. Regioselective ring-opening of epoxides triggered by light[J]. Chinese Journal of Catalysis, 2026, 85: 34-46.

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Photocatalytic epoxide alcoholysis
Catalyst	Light		T			Nucleophile		Substrate		Atmosphere			Regioselectivity (α:β) ^a			Rate (mmol/(g·h))		Ref.
Cs₃Bi₂Br₉	Xe lamp >420 nm		20 °C			i-PrOH		styrene oxide		Air			90% (α)			1.3		[6]
CuPd/TiO₂	Xe lamp		r.t.^b			MeOH		styrene oxide		Ar			>99% (α)			176		[29]
ZIS₁@CdS	Xe lamp >420 nm		40 °C			i-PrOH		styrene oxide		Air			>99% (α)			87		[5]
ZIS₁@CdS	Xe lamp >420 nm		40 °C			i-PrOH		epichlorohydrin		Air			>99% (β)			1.8		[5]
MS/ZIS	Xe lamp		50 °C			i-PrOH		styrene oxide		Air			>95% (α)			582.6		[7]
Photocatalytic epoxide deoxygenation
Catalyst	Light		T		Nucleophile		Substrate			Atmosphere		Yield (Selectivity)				AQY (wavelength)		Ref.
TiO₂	Xe lamp >300 nm		30 °C		i-PrOH		styrene oxide			N₂		95% (95%)				8.5% (300 nm)		[30]
Au/CeO₂	Halogen lamp		30 °C		i-PrOH		styrene oxide			Ar		20% (88%)				n/a^c		[36]
Photocatalytic epoxide hydrogenolysis
Catalyst	Light	T		Electron donor					HTC^d		Regioselectivity (α:β) ^a			Substrate	Atmosphere		Yield	Ref.
Pt₂/TiO₂	Xe lamp >300 nm	30 °C		i-PrOH					Pt		n/a			trans-stilbene oxide	N₂		>99%	[39]
Cp₂TiCl₂	green LED	r.t.		iPr₂NEt					methyl thioglycolate		>99% (α)			oxirane	Ar		85%	[31]
Au/TiO₂	365 nm	25 °C		THF^e					Pd(OAc)₂		>99% (α)			styrene oxide	N₂		49%	[53]
Cp₂Zr(OTf)₂·THF	blue LED	35 °C		Ir(4-MeO-ppy)₃					cyclohexadiene		80% (β)			styrene oxide	N₂		90%	[40]
VB₁₂	427 nm	r.t.		Zn/NH₄Cl					TRIP Thiol ^f		95% (β)			styrene oxide	N₂		84%	[41]
Photocatalytic epoxide carboxylation
Catalyst	Light	T		Electron donor					base		Substrate			atmosphere	regioselectivity (α:β)^a		Yield	Ref.
4CzTPN	blue LED	r.t.		DIPEA ^g					Cs₂CO₃		Aryl epoxides			CO₂	>99% (α)		75%	[17]
Photocatalytic epoxide arylation
Catalyst	Light	T		Substrate					Ligands		Nucleophile			Atmosphere	Regioselectivity (α:β)^a		Yield	Ref.
VB₁₂/NiCl₂	blue LED	r.t.		styrene oxide					n/a		I-Ar			N₂	>99% (β)		60%	[54]
Cp₂TiCl₂/NiBr₂	blue LED	r.t.		epoxybutane					t-Bu-terpy		I-Ar			N₂	>99% (β)		48%	[9]
Cp₂TiCl₂/NiBr₂	blue LED	r.t.		styrene oxide					2-pyridine-methanimine		I-Ar			N₂	>99% (α)		82%	[9]
4CzIPN/NiBr₂	blue LED	r.t.		styrene oxide					chiral bilm		I-Ar			N₂	>99% (β)		70%	[32]
Photocatalytic epoxide allylation
Catalyst	Light	T		substrate					Electron donor		Allylating reagent			Atmosphere	Regioselectivity		Yield	Ref.
4CzIPN/NiCl₂(bpy)	blue LED	r.t.		oxabenzon-orbornadienes					Et₃N		allyl acetate			N₂	n/a		70%	[10]
4CzIPN/ NiCl₂(bpy)	blue LED	r.t.		oxabenzon-orbornadienes					Et₃N		vinylic cyclic carbonates			N₂	n/a		69%	[10]

Photocatalytic epoxide alcoholysis
Catalyst	Light		T			Nucleophile		Substrate		Atmosphere			Regioselectivity (α:β) ^a			Rate (mmol/(g·h))		Ref.
Cs₃Bi₂Br₉	Xe lamp >420 nm		20 °C			i-PrOH		styrene oxide		Air			90% (α)			1.3		[6]
CuPd/TiO₂	Xe lamp		r.t.^b			MeOH		styrene oxide		Ar			>99% (α)			176		[29]
ZIS₁@CdS	Xe lamp >420 nm		40 °C			i-PrOH		styrene oxide		Air			>99% (α)			87		[5]
ZIS₁@CdS	Xe lamp >420 nm		40 °C			i-PrOH		epichlorohydrin		Air			>99% (β)			1.8		[5]
MS/ZIS	Xe lamp		50 °C			i-PrOH		styrene oxide		Air			>95% (α)			582.6		[7]
Photocatalytic epoxide deoxygenation
Catalyst	Light		T		Nucleophile		Substrate			Atmosphere		Yield (Selectivity)				AQY (wavelength)		Ref.
TiO₂	Xe lamp >300 nm		30 °C		i-PrOH		styrene oxide			N₂		95% (95%)				8.5% (300 nm)		[30]
Au/CeO₂	Halogen lamp		30 °C		i-PrOH		styrene oxide			Ar		20% (88%)				n/a^c		[36]
Photocatalytic epoxide hydrogenolysis
Catalyst	Light	T		Electron donor					HTC^d		Regioselectivity (α:β) ^a			Substrate	Atmosphere		Yield	Ref.
Pt₂/TiO₂	Xe lamp >300 nm	30 °C		i-PrOH					Pt		n/a			trans-stilbene oxide	N₂		>99%	[39]
Cp₂TiCl₂	green LED	r.t.		iPr₂NEt					methyl thioglycolate		>99% (α)			oxirane	Ar		85%	[31]
Au/TiO₂	365 nm	25 °C		THF^e					Pd(OAc)₂		>99% (α)			styrene oxide	N₂		49%	[53]
Cp₂Zr(OTf)₂·THF	blue LED	35 °C		Ir(4-MeO-ppy)₃					cyclohexadiene		80% (β)			styrene oxide	N₂		90%	[40]
VB₁₂	427 nm	r.t.		Zn/NH₄Cl					TRIP Thiol ^f		95% (β)			styrene oxide	N₂		84%	[41]
Photocatalytic epoxide carboxylation
Catalyst	Light	T		Electron donor					base		Substrate			atmosphere	regioselectivity (α:β)^a		Yield	Ref.
4CzTPN	blue LED	r.t.		DIPEA ^g					Cs₂CO₃		Aryl epoxides			CO₂	>99% (α)		75%	[17]
Photocatalytic epoxide arylation
Catalyst	Light	T		Substrate					Ligands		Nucleophile			Atmosphere	Regioselectivity (α:β)^a		Yield	Ref.
VB₁₂/NiCl₂	blue LED	r.t.		styrene oxide					n/a		I-Ar			N₂	>99% (β)		60%	[54]
Cp₂TiCl₂/NiBr₂	blue LED	r.t.		epoxybutane					t-Bu-terpy		I-Ar			N₂	>99% (β)		48%	[9]
Cp₂TiCl₂/NiBr₂	blue LED	r.t.		styrene oxide					2-pyridine-methanimine		I-Ar			N₂	>99% (α)		82%	[9]
4CzIPN/NiBr₂	blue LED	r.t.		styrene oxide					chiral bilm		I-Ar			N₂	>99% (β)		70%	[32]
Photocatalytic epoxide allylation
Catalyst	Light	T		substrate					Electron donor		Allylating reagent			Atmosphere	Regioselectivity		Yield	Ref.
4CzIPN/NiCl₂(bpy)	blue LED	r.t.		oxabenzon-orbornadienes					Et₃N		allyl acetate			N₂	n/a		70%	[10]
4CzIPN/ NiCl₂(bpy)	blue LED	r.t.		oxabenzon-orbornadienes					Et₃N		vinylic cyclic carbonates			N₂	n/a		69%	[10]

光催化环氧化合物的区域选择性开环反应

Regioselective ring-opening of epoxides triggered by light

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