Premium
Regioselective Synthesis of Polyheterohalogenated Naphthalenes via the Benzannulation of Haloalkynes
Author(s) -
Lehnherr Dan,
Alzola Joaquin M.,
Lobkovsky Emil B.,
Dichtel William R.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503418
Subject(s) - regioselectivity , naphthalene , derivatization , modularity (biology) , combinatorial chemistry , halide , chemistry , organic synthesis , organic chemistry , catalysis , high performance liquid chromatography , biology , genetics
Independent control of halide substitution at six of the seven naphthalene positions of 2‐arylnaphthalenes is achieved through the regioselective benzannulation of chloro‐, bromo‐, and iodoalkynes. The modularity of this approach is demonstrated through the preparation of 44 polyheterohalogenated naphthalene products, most of which are difficult to access through known naphthalene syntheses. The outstanding regioselectivity of the reaction is both predictable and proven unambiguously by single‐crystal X‐ray diffraction for many examples. This synthetic method enables the rapid preparation of complex aromatic systems poised for further derivatization using established cross‐coupling methods. The power and versatility of this approach makes substituted naphthalenes highly attractive building blocks for new organic materials and diversity‐oriented synthesis.