A Reiterative Approach to 2,3-Disubstituted Naphthalenes and Anthracenes

Abstract

[reaction: see text] Simple bis(bromoethynyl)arenediynes are easily prepared by the desilylative halogenation of the corresponding trimethylsilyl derivatives. Cycloaromatization of these halogenated enediynes leads to the otherwise difficult to prepare 2,3-dibromoarenes in good yield. Alkynylation of the resulting haloaromatic compound regenerates the soluble enediyne system, homologated by one aromatic ring. This iterative methodology can be terminated by the cycloaromatization of the unsubstituted enediyne, providing the simple acene hydrocarbon.

Triazole: a unique building block for the construction of functional materials

“…4,5 The Diels-Alder and cyclotrimerisation reactions 3 (orange), belonging to the pool of cycloaddition reactions, together with the Bergman cyclisation reaction [11][12][13] (red) represent the main tools for the construction of benzenoid cutouts of graphene, such as polycyclic aromatic hydrocarbons (PAHs). 14 …”

“…Conjugation-related representative examples of triazole-derived oligomeric(8)(9)(10)(11)(12)(13)(14) and polymeric(15)(16)(17)(18)(19)(20)(21) structures as potential materials for organic optoelectronics.…”

Rhodium/Phosphine/Amine⋅HBr Catalyst System for Highly Selective Cross‐Cyclodimerization of Aryl‐ and Alkylalkynes: Efficient Access to Multisubstituted Naphthalene Derivatives

“…In particular, those with polycyclic p-conjugated structures have recently become increasingly important in the area of organic electronics. [1] The transition-metalmediated annulative benzene ring homologation with alkynes or their equivalents [2][3][4][5][6] is one of the modern potential synthetic strategies to prepare naphthalenes and higher fused aromatics. As one of the early examples, Sakakibara [2a] and Heck [2b] independently reported the palladium-catalyzed annulation reaction of aryl halide with two acetylenedicarboxylate or diphenylacetylene molecules to construct the naphthalene skeletons.…”

Synthesis and reactivity of anthracenyl-substituted arenediynes

“…12,[14][15][16] Moreover, the photophysical properties of polycyclic aromatic hydrocarbons containing the 5-membered ring are unusual compared to the analogous molecules with 6-membered rings. 3,[5][6][7][8][9][10][11][12][13]15 It is thus of interest to develop a better understanding of the structure-property relationships of the 5-membered ring containing polycyclic aromatic hydrocarbons. Cyclization of arylsubstituted arenediynes proceeds via C 1 -C 5 cyclization (5-membered cyclic product) or C 1 -C 6 Bergman cyclization (6-membered cyclic product) pathway that can be modulated by the sterics and electronics of aryl substituents.…”