/ Practical synthesis of polysubstituted naphthalene derivatives via HNTf2-catalyzed benzannulation reaction
Issue in Honor of Dr. Jhillu S. Yadav ARKIVOC 2016 (ii) 62-81 Practical synthesis of polysubstituted naphthalene derivatives via HNTf2-catalyzed benzannulation reaction Sudipta Ponra, Maxime R. Vitale,* Véronique Michelet,* and Virginie Ratovelomanana-Vidal* PSL Research University, Chimie ParisTech - CNRS, Institut de Recherche de Chimie Paris, 75005, Paris, France E-mail: maxime.vitale@chimie-paristech.fr, veronique.michelet@chimie-paristech.fr, virginie.vidal@chimie-paristech.fr Dedicated to Professor J. S. Yadav on the occasion of his 65th birthday DOI: http://dx.doi.org/10.3998/ark.5550190.p009.219 Abstract The synthesis of polysubstituted naphthalenes using the triflimide-catalyzed benzannulation of arylacetaldehydes with alkynes at room temperature is described. This method demonstrates a high functional group tolerance and, in the case of halogen substituted naphthalenes, opens the route for further functionalization by palladium-catalyzed cross-coupling reactions. With an analogous organocatalytic strategy, arylepoxides or 2-arylacetal derivatives are also suitable partners in the related benzannulation reactions with aryl-alkynes. Keywords: Organocatalysis, naphthalene, benzannulation, triflimide Introduction Substituted naphthalene derivatives are important pharmacophores in many biologically active compounds which possess anti-inflammatory, antibacterial, antimicrobial and anticancer activities.1-9 Additionally, this particular aromatic structure can be found in numerous optical and electronic materials10-12 and constitutes the backbone of many chiral ligands.13 Nafacillin,14 suramin,15,16 which play a vital role in the control of microbial infection, are typical examples of drugs that present a naphthalene moiety (Figure 1). Therefore, the development of new and efficient methods for the synthesis of naphthalene skeletons has been a subject of great interest in recent years.17-42 Most of the traditional approaches toward naphthalene derivatives involve the stepwise introduction of a substituent through electrophilic substitution or coupling reactions.17,18 Construction of the second aromatic ring of the naphthalene core via a formal [4+2] process Page 62 © ARKAT-USA, Inc.
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