Recent Progress in the Synthesis of Dendralenes: A Decade Update

doi:10.6023/cjoc202008024

Abstract

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

Cite this article

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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Fig. & Tab. 28

Figure 1. Representative fundamental classes of conjugated oligo-alkenes

Figure 2. Representative development of dendralenes

Scheme 1. Synthesis of dendralenes through two fold Negishi couplings

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

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

Scheme 4. Synthesis of dendralenes from substituted cumulative alkenes

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

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

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

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

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

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

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

Scheme 12. Constructions of chiral spiro[3]dendralenes

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

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

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

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

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

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

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

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

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

Scheme 22. Palladium-catalyzed selective cascade reaction of bisallenes

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

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

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

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

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近十年Dendralenes催化合成研究进展