Synthesis, Cross-Coupling, and Anionic Cyclization of ortho-Substituted Naphthaleneboronic Esters

Synthesis, Cross-Coupling, and Anionic Cyclization of ortho-Substituted Naphthaleneboronic Esters

Abstract 1-Fluoro-, 1-chloro- and 1-cyanonaphthalene were lithiated and then borylated at the 2-position. The 1-substituted naphthaleneboronic esters were cross-coupled with aryl halides to give 2-aryl-1-fluoro-, 2-aryl-1-chloro- and 2-aryl-1-cyanonaphthalenes. The 2-aryl-1-cyano- and 2-aryl-1-fluor...

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Veröffentlicht in:Synthesis (Stuttgart) 2006-10, Vol.2006 (20), p.3478-3484
Hauptverfasser: Lysén, Morten, Madden, Maurice, Kristensen, Jesper Langgaard, Vedsø, Per, Zøllner, Camilla, Begtrup, Mikael
Format: Artikel
Sprache:eng
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Zusammenfassung:Abstract 1-Fluoro-, 1-chloro- and 1-cyanonaphthalene were lithiated and then borylated at the 2-position. The 1-substituted naphthaleneboronic esters were cross-coupled with aryl halides to give 2-aryl-1-fluoro-, 2-aryl-1-chloro- and 2-aryl-1-cyanonaphthalenes. The 2-aryl-1-cyano- and 2-aryl-1-fluoronaphthalenes were reacted with N-butyllithium or lithium morpholide to give new benzophen­anthridine derivatives.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2006-950239