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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-ca talyzed cross-coupling reactions. With an analogous organocatalytic strategy, arylepoxides or 2-arylacetal derivatives are also suitable partners in the related benzannulation reactions wi th aryl-alkynes.
Highlights
Substituted naphthalene derivatives are important pharmacophores in many biologically active compounds which possess anti-inflammatory, antibacterial, antimicrobial and anticancer activities.[1,2,3,4,5,6,7,8,9] this particular aromatic structure can be found in numerous optical and electronic materials[10,11,12] and constitutes the backbone of many chiral ligands.[13]
We recently discovered that triflimide (HNTf2)[43,44,45,46,47] is an efficient catalyst for the benzannulation of arylacetaldehyde derivatives with alkynes.[48]
We report a more detailed study of this benzannulation reaction for the synthesis of a larger number of naphthalene derivatives displaying various useful functionalities
Summary
Substituted naphthalene derivatives are important pharmacophores in many biologically active compounds which possess anti-inflammatory, antibacterial, antimicrobial and anticancer activities.[1,2,3,4,5,6,7,8,9] this particular aromatic structure can be found in numerous optical and electronic materials[10,11,12] and constitutes the backbone of many chiral ligands.[13]. The development of new and efficient methods for the synthesis of naphthalene skeletons has been a subject of great interest in recent years.[17,18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33,34,35,36,37,38,39,40,41,42] 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 under various catalytic conditions is definitely one of the most direct and efficient methods.[19,20,21,22,23,24,25,26,27,28,29,30,31,32,33,34,35,36,37,38,39,40,41,42]
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