ChemInform Abstract: Directed ortho Metalation Strategies. Effective Regioselective Routes to 1,2‐, 2,3‐, and 1,2,3‐Substituted Naphthalenes.

Abstract

Directed ortho Metalation Strategies. Effective Regioselective Routes to 1,2-, 2,3-, and 1,2,3-Substituted Naphthalenes. -Directed ortho-metalation of naphthyl--2-carbamate followed by reaction with various electrophiles affords di-and trisubstituted naphthalenes with high regioselectivity. Further derivatization of product (XIV) via ipso-halodesilylation provides dihalonaphthalene (XV). A three step sequence involving Suzuki-Miyaura coupling, Fries rearrangement, and cyclization allows the conversion of product (XIV) into benzonaphthopyranones (XIX). -(GROOM, K.; HUSSAIN, S. M. S.; MORIN, J.; NILEWSKI, C.; RANTANEN, T.; SNIECKUS*, V.; Org. Lett. 16 (2014) 9, 2378-2381, http://dx.doi.org/10.1021/ol500707w ; Dep. Chem., Queen's Univ., Kingston, Ont. K7L 3N6, Can.; Eng.) -Mais 46-051