异腈参与的光催化反应研究进展

doi:10.6023/cjoc202206012

摘要/Abstract

异腈是一类有价值的C1结构单元, 广泛应用于有机化学、组合化学、生物医药等领域, 其衍生物更是构建生物活性分子和复杂的天然产物的有效模块. 根据异腈参与光催化反应的机制进行分类, 综述了近五年异腈参与光催化反应的研究进展, 着重讨论了光催化剂、底物适用性以及反应机制, 并对该领域存在的挑战以及未来发展趋势进行了浅谈和展望.

关键词: 异腈, 可见光催化, 协同光催化, 可见光诱导的过渡金属催化

Isocyanides are a class of valuable C1 building blocks, widely used in organic chemistry, combinatorial chemistry, biomedicine and other fields, and their derivatives are effective building blocks for the synthesis of bioactive molecules and complex natural products. Herein, the recent advances in photocatalytic reactions with isocyanides are summarized according to the types of the reaction mechanism. The photocatalyst, substrate range and reaction mechanism are emphatically discussed. Finally, the challenges and future development trends of this research field are discussed and prospected.

Key words: isocyanide, visible light photocatalysis, cooperative photocatalysis, transition metal-based photocatalyst

引用此文

何燕, 黄天姿, 史小琴, 陈艳, 吴琼. 异腈参与的光催化反应研究进展[J]. 有机化学, 2022, 42(12): 4220-4246.

Yan He, Tianzi Huang, Xiaoqin Shi, Yan Chen, Qiong Wu. Recent Advances in Photocatalytic Reactions with Isocyanides[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4220-4246.

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图/表 33

图1. 可见光催化在有机合成中的发展历程

Figure 1. Development history of visible light catalysis in organic synthesis

图2. 通过(a)常规光催化、(b)协同光催化和(c)可见光诱导的过渡金属催化实现的可见光诱导转化

Figure 2. Visible light-induced transformations via (a) conventional photocatalysis, (b) cooperative photocatalysis, and (c) visible light-induced transition metal catalysis

图3. 光催化机理

Figure 3. Mechanisms of photocatalysis

图式1. 可见光诱导的SET路径

Scheme 1. Visible-light-induced SET pathways

Entry	Photocatalyst	E_1/2(M⁺/M*)/V	E_1/2(M*/M^–)/V	E_1/2(M⁺/M)/V	E_1/2(M/M^–)/V	Ref.
1	fac-Ir(ppy)₃	–1.73	+0.31	+0.77	–2.19	[13]
2	Ir[dF(CF₃)ppy]₂(dtb-bpy)⁺	–0.89	+1.21	+1.69	–1.37	[14]
3	[Ir(ppy)₂(dtbbpy)]⁺	–0.96	+0.66	+1.21	–1.51	[14,15]
4	Ru(bpy)₃²⁺	–0.81	+0.77	+1.29	–1.33	[16]
5	Cz-NI	–1.67	+1.28	+1.01	–1.40	[17]
6	MANI	–1.67	+1.11	+0.99	–1.55	[17]
7	Rose Bengal	–0.68	+0.99	+1.09	–0.78	[18]
8	Eosin Y	–1.60	+1.18	+0.72	–1.14	[18]

表1. 常用可见光光催化剂的氧化还原电位a

Table 1. Redox potentials of commonly utilized visible light photocatalysts

图4. 通过SET路径进行光化学反应代表性催化剂

Figure 4. Representative catalysts for photochemical reactions through SET pathways

图式2. 铱催化光氧化还原介导的自由基机制合成2-芳基或2-苯硫基吲哚乙基3-乙醛酸酯

Scheme 2. Ir-catalyzed photoredox-mediated radical process to synthesize 2-aryl or 2-phenylthio-indoleethyl 3-glyoxylates

图式3. 可见光诱导芳基异腈和环丁酮肟酯的自由基级联环化反应用于合成环戊-[b]喹喔啉

Scheme 3. A visible-light-induced radical cascade cyclization of aryl isonitriles and cyclobutanone oxime esters for the synthesis of cyclopenta-[b]quinoxalines

图式4. 可见光诱导的铱配合物催化2-异腈芳基硫醚的自由基级联环化反应

Scheme 4. A visible-light-induced radical cascade cyclization of 2-isocyanoaryl thioethers

图式5. 可见光诱导铱催化2-烯基芳基异腈与α-氧代羧酸的脱羧环化反应

Scheme 5. Iridium-catalyzed visible lightinduced decarboxylative cyclization of 2-alkenylarylisocyanides with α-oxocarboxylic acids

图式6. 可见光诱导铱催化异腈化合物的自由基二氟甲基化用于合成二氟甲基菲和异喹啉

Scheme 6. Iridium-catalyzed visible-light-driven radical difluoromethylation of isocyanides to access difluoromethylated phenanthridines and isoquinolines

图式7. 异腈化合物的可见光光催化功能化合成仲酰胺和乙烯酮胺类化合物

Scheme 7. Visible-light photocatalytic functionalization of isocyanides for the synthesis of secondary amides and ketene aminals

图式8. 光催化异腈化合物的多组分多米诺级联反应

Scheme 8. Photocatalytic isocyanide-based multicomponent domino cascade reaction

图式9. 可见光诱导3-(2-异腈基苄基)吲哚与溴二氟乙酸盐或溴二氟乙酰胺之间的自由基插入反应

Scheme 9. Visible-light-induced radical isocyanide insertion reactions between 3-(2-isocyanobenzyl)-indoles and bromodifluoroacetates or bromodifluoroacetamides

图式10. 可见光诱导铱催化异腈和黄原酸盐为原料高效合成6-烷基化菲啶的新方法

Scheme 10. Synthesis of 6-alkylated phenanthridines using xanthates as radical precursors under visiblelight photoredox catalysis

图式11. 可见光诱导邻二异腈基芳烃的自由基级联环化反应用于合成苯并[a]吩嗪

Scheme 11. A visible-light-induced radical cascade cyclization of ortho-diisocyanoarenes for the synthesis of diethyl benzo[a]phenazine-6,6(5H)-dicarboxylates

图式12. 可见光诱导铑配合物催化芳硫基二氟烷基2-吡啶基砜与异腈高效合成菲啶和异喹啉化合物

Scheme 12. Visible-light-induced, Rh-catalyzed cyclization of arylthiodifluoromethyl 2-pyridyl sulfone with isocyanides for the synthesis of phenanthridines

图式13. 可见光催化合成喜树碱基本骨架

Scheme 13. Visible-light-mediated protocol for the synthesis of ring cores of camptothecins

图式14. 可见光催化合成6-烷基化菲啶衍生物

Scheme 14. Visible-light-mediated protocol for the synthesis of 6-alkylated phenanthridine derivatives

图式15. 可见光诱导锰催化2-联苯异腈与环丙醇的串联环化合成6-β-酮烷基菲

Scheme 15. Visible-light-induced, manganese-catalyzed tandem cyclization of 2-biphenyl isocyanides with cyclopropanols for the synthesis of 6-β-ketoalkyl phenanthridines

图式16. 可见光诱导Rose Bengal催化异腈、硫醇和水合成硫代氨基甲酸酯化合物

Scheme 16. Visible-light-enabled construction of thiocarbamates from isocyanides, thiols and water

图式17. 可见光和空气促进的2-异腈基联苯的自由基硫氰化反应用于合成 6-硫氰基菲啶

Scheme 17. Synthesis of 6-thiocyanatophenanthridines by visible-light- and air-promoted radical thiocyanation of 2-isocyanobiphenyls

图式18. 可见光诱导异腈、α-氧代羧酸和水的脱羧酰化反应

Scheme 18. Visible-light-mediated metal-free decarboxylative acylations of isocyanides with α-oxocarboxylic acids and water leading to α-ketoamides

图式19. 可见光诱导Rose Bengal催化2-异腈基芳基硫醚的磷酸化反应

Scheme 19. Visible-light-mediated Rose Bengal-catalyzed phosphorylation of 2-isocyanoaryl thioethers

图式20. Eosin Y催化苯乙烯、2-氨基嘧啶和异腈酸叔丁酯的多组分反应

Scheme 20. Eosin Y-catalyzed multicomponent reaction of styrene, 2-aminopyrimidine and tert-butyl isocyanide

图式21. 有机染料Eosin Y催化烯基苯胺和异腈的环化反应

Scheme 21. Eosin Y-catalyzed cyclization of o-alkenylanilines and isocyanides

图式22. fac-Ir(ppy)3催化异腈参与的SET和EnT协同机制

Scheme 22. fac-Ir(ppy)3-catalyzed isonitrile-involved SET and EnT synergistic mechanism

图式23. 通过HAT机制合成咪唑并[1,2-a]吡啶

Scheme 23. Synthesis of 3-aminoimidazo[1,2-a]pyridines via the HAT mechanism

图式24. 可见光诱导[Ru(bpy)3](PF6)2催化2-烯基芳基异腈化合物和硫醇的自由基级联反应

Scheme 24. Photoredox catalysis toward 2?sulfenylindole synthesis through a radical cascade process

图式25. Cz-NI催化诱导饱和氮杂杂环的无金属α-C(sp3)—H氨基甲酰化反应

Scheme 25. Photoinduced metal-free α-C(sp3)—H carbamoylation of saturated aza-heterocycles via Cz-NI organic photocatalyst

图式26. 4CzIPN-tBu为光催化剂诱导磷自由基引发的异腈级联环化反应

Scheme 26. 4CzIPN-tBu-catalyzed proton-coupled electron transfer for photosynthesis of phosphorylated N?heteroaromatics

图式27. 三组分协同光催化烯烃1,2-烷基氨基甲酰化/氰化反应

Scheme 27. Visible light-promoted dual nickel- and photoredox catalyzed spirocyclization of isocyanides with 1,5-enynes

图式28. 可见光诱导钯催化烯烃、烷基碘和异腈三组分1,2-烷基官能化反应

Scheme 28. Visible-light-induced Pd-catalyzed three-component 1,2-alkyl functionalization of alkenes with alkyl iodides and isocyanides

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