近十年Dendralenes催化合成研究进展

doi:10.6023/cjoc202008024

摘要/Abstract

Dendralenes作为一种含有支链骨架的交叉共轭聚烯烃, 是多种天然产物和光电材料的基本骨架, 也是快速构建手性多环结构的重要中间体, 在功能材料、天然产物化学、聚合物化学和合成化学等诸多领域占据重要地位. Dendralenes的合成与衍生化应用是一个曾经被忽视但正在兴起的领域. 近年来, dendralenes的合成得到了较快发展, 按dendralenes共轭单元数的不同概述了其合成领域的最新成果, 重点介绍反应设计与机理, 并展望了dendralenes的后续合成与应用研究发展.

关键词: Dendralenes, 共轭低聚烯烃, 累积烯烃, 偶联, 环化, 衍生化

Dendralenes, also known as acyclic, branched and cross-conjugated polyenes, represent an important class of hydrocarbons. Serving as basic motifs for a number of natural products and photolectric materials as well as key intermediates in the rapid synthesis of polycyclic compounds, dendralenes have recently played a prominent part in the area of material chemistry, polymer chemistry, synthetic chemistry and so on. The study on dendralenes has long been neglected but received renewed attention and witnessed rapid development in recent years. The advanced syntheses of dendralenes in the last decade are summarized and organized in order of the number of conjugated units. The synthetic design and mechanism are highlighted in this review with their future development on synthesis and application proposed as well.

Key words: dendralenes, conjugated polyenes, cumulenes, coupling, cyclization, derivate

引用此文

祝洁, 杨文超, 张乘运, 吴磊. 近十年Dendralenes催化合成研究进展[J]. 有机化学, 2021, 41(3): 1081-1097.

Jie Zhu, Wenchao Yang, Chengyun Zhang, Lei Wu. Recent Progress in the Synthesis of Dendralenes: A Decade Update[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1081-1097.

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图/表 28

图1. 代表性共轭低聚烯烃的基本类别

Figure 1. Representative fundamental classes of conjugated oligo-alkenes

图2. Dendralenes代表性发展历程

Figure 2. Representative development of dendralenes

图式1. 两次Negishi偶联合成dendralenes

Scheme 1. Synthesis of dendralenes through two fold Negishi couplings

图式2. HWE反应合成[3]dendralenes及其高区域选择性Diels-Alder反应研究

Scheme 2. Synthesis of [3]dendralenes through HWE reactions and their Diels-Alder reactions with unexpected regioselectivity

图式3. 3-溴-2,4-戊二烯基三甲基硅烷用于合成[3]dendralenes及其环化反应制备多环化合物

Scheme 3. 3-Bromopenta-2,4-dienylsilane as reagent for the preparation of [3]dendralenes and their cycloaddition reactions toward polycyclic compounds

图式4. 累积烯烃用于dendralenes的构建

Scheme 4. Synthesis of dendralenes from substituted cumulative alkenes

图式5. 铑催化导向基团辅助的烯烃C—H键活化以及与联烯丙基醋酸酯的偶联反应合成[3]dendralenes

Scheme 5. Rhodium(III)-catalyzed alkenyl C—H activation and coupling reaction with allenyl carbinol carbonate to construct [3]dendralenes

图式6. 钯催化联烯丙基C—H键氧化与分子间C—C键形成构建[3]dendralenes

Scheme 6. Pd-catalyzed allenic C—H bond oxidation and intermolecular C—C bond formation for the synthesis of [3]dend- ralenes

图式7. 钯催化的去单芳酰基二聚合成[3]dendralenes

Scheme 7. Palladium-catalyzed monodearoylative dimerization approach for the synthesis of [3]dendralenes

图式8. 钯催化磷酰基取代联烯与N-苯磺酰腙的偶联反应合成膦酰基[3]dendralenes

Scheme 8. Palladium-catalyzed coupling of allenylphosphine oxides with N-tosylhydrazones toward phosphinyl [3]dendralenes

图式9. 金属组分控制的立体选择性氢化合成膦氧取代(Z)-[3]dendralenes

Scheme 9. Metal components-controlled regioselective hydrogenation toward phosphinyl (Z)-[3]dendralenes

图式10. 炔基化、选择性氢化串联反应合成膦酰基(Z)-[3]dendralenes

Scheme 10. Cascade alkynylation and selective hydrogenation to access phosphinyl (Z)-[3]dendralenes

图式11. 铜催化炔烃的烯丙基硼化构筑硼化[3]dendralenes

Scheme 11. Copper catalyzed allylboration of alkynes for the synthesis of borylated [3]dendralenes

图式12. 手性螺环[3]dendralenes的构建

Scheme 12. Constructions of chiral spiro[3]dendralenes

图式13. KTC以及Negishi偶联反应制备[3]~[8]dendralenes

Scheme 13. Practical syntheses of [3]~[8]dendralenes using KTC and Negishi couplings

图式14. [2+2]环加成/开环反应制备[n]dendralenes

Scheme 14. Synthesis of [n]dendralenes through [2+2] cycloaddition/cycloreversion cascades

图式15. 四氰基乙烯与四芳基累积[5]烯烃的加成反应合成[4]轴烯和denedralenes

Scheme 15. Formation of [4]radialene and dendralenes by addition of tetracyanoethylene to tetraaryl[5]cumulene

图式16. 双偶联合成[n]dendralenes及[3]~[12]dendralenes化学性质分析

Scheme 16. Double-cross coupling approach for the synthesis of [n]dendralenes and the analysis on chemical properties of [3]~[12]dendralenes

图式17. 电环化开环合成端位取代[3]~[4]dendralenes

Scheme 17. Synthesis of terminally substituted [3]~[4]den- dralenes through electrocyclic ring-opening reaction

图式18. 钯催化取代联烯酸酯的偶联反应合成功能化[3]~[6]dendralenes

Scheme 18. Synthesis of functionalized [3]~[6]dendralenes through palladium-catalyzed cross-couplings of substituted allenoates

图式19. Dendralenes中C—C单键的旋转

Scheme 19. Rotation of C—C bond in dendralenes molecules

图式20. 底物控制(a)和反应条件控制(b)的钯催化联烯炔的硼化、碳环化反应

Scheme 20. Palladium-catalyzed borylating carbocyclizations of allenynes with (a) structural difference determined selectivity and (b) reaction conditions controlled selectivity

图式21. 联烯炔碳环化反应构建环化[3]dendralenes

Scheme 21. Carbocyclization of allenynes for the construction of cyclo-[3]dendralenes

图式22. 催化双联烯的选择性串联反应

Scheme 22. Palladium-catalyzed selective cascade reaction of bisallenes

图式23. 联烯炔/双联烯分子内环化构建环化dendralenes

Scheme 23. Construction of cyclo-dendralenes with allenynes or bisallenes through intermolecular cyclization

图式24. Ru催化的烯丙基化-环化反应构建环化[3]dendra- lenes及串联反应制备复杂多环化合物

Scheme 24. Ruthenium-catalyzed allylation-cyclization reactions for the synthesis 2,3-cyclo[3]dendralenes and cascade reactions toward complex polycyclic compounds

图式25. Rh催化的联烯与炔烃的环化三聚/二聚反应

Scheme 25. Rhodium-catalyzed cyclotrimerization and dimerization of allenes with alkynes

图式26. 钯催化联烯酯[4+3]环加成/偶联反应构建[3]den- dralenes

Scheme 26. Palladium-catalyzed [4+3] cycloaddition/cross- coupling of allenic esters to construct [3]dendralenes

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