Metal-free remote-site C–H alkenylation: regio- and diastereoselective synthesis of solvatochromic dyes

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Title: Metal-free remote-site C–H alkenylation: regio- and diastereoselective synthesis of solvatochromic dyes
Authors: Albaladejo Maricó, María José | González Soria, María José | Alonso, Francisco
Research Group/s: Nuevos Materiales y Catalizadores (MATCAT)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Metal-free remote-site | C–H alkenylation | Regio- and diastereoselective synthesis | Solvatochromic dyes
Knowledge Area: Química Orgánica
Issue Date: 2018
Publisher: Royal Society of Chemistry
Citation: Green Chemistry. 2018, 20: 701-712. doi:10.1039/C7GC03436A
Abstract: Lately, transition-metal catalysed C–H alkenylation of nitrogen heterocycles has gained increasing attention, often with the intervention of complex and expensive catalytic systems. On the other hand, both, chalcones and indolizines are versatile families of compounds with applications in diverse research areas, including materials science, because of their prominent photophysical attributes. We set forth herein the metal-free regio- and diastereoselective C–H alkenylation of indolizines through a very simple and mild acid–base approach. The most fascinating fact in this remote-site Csp2–Csp2 bond formation is that only one starting material is utilised, which undergoes a formal self-alkenylation to integrate a chalcone moiety and furnish a new family of dyes; a plausible reaction mechanism has been put forward. A one-pot multicomponent protocol was conceived that generates the starting indolizine in situ and has been extended to a multi-gram scale synthesis with equal efficiency. The dyes show a single structure in the solid state but two stable structures in solution (rotamers). Preliminary studies on the optical properties of the dyes reveal a particle-size dependent colour in the solid state and solvatochromism (i.e., different colours in solution depending on the solvent polarity). Remarkably, the solvatochromic behaviour was also displayed in plastics. We believe that this finding opens new avenues in the fields of heterocyclic chemistry, dyes, and materials science.
Sponsor: This work was generously supported by the Spanish Ministerio de Economía y Competitividad (MINECO; CTQ2011-24151 and CTQ-2015-66624-P) and the Generalitat Valenciana (GV; grants no. APOTIP/2015/014 and AEST/2015/001). M. J. A. and M. J. G.-S. are grateful to the Instituto de Síntesis Orgánica (ISO) for both pre-doctoral grants (contracts no. I-PAS-44/13 and I-PAS-11/16).
ISSN: 1463-9262 (Print) | 1463-9270 (Online)
DOI: 10.1039/C7GC03436A
Language: eng
Type: info:eu-repo/semantics/article
Rights: © The Royal Society of Chemistry 2018
Peer Review: si
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Appears in Collections:INV - MATCAT - Artículos de Revistas

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