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1-Naphthaleneboronic acid is a very useful building block for introduction of a naphthyl group through cross-coupling protocols. It is useful in the synthesis of polyaromatic hydrocarbons utilizing the Suzuki reaction.
Cheng-Hsien Yang; Chia-Cheng Tai; Yu-Ting Huang; I-Wen Sun. Ionic liquid promoted palladium-catalyzed Suzuki cross-couplings of N-contained heterocyclic chlorides with naphthaleneboronic acids. Tetrahedron.2005, 61 4857-4861.
R. L. Letsinger; J. Malcolm Smith; J. Gilpin; D. B. MacLean. Organoboron Compounds. XX. Chemistry of Some 1-Naphthaleneboronic Acids with Substituents in the 8-Position. J. Org. Chem.1965, 30 (3), 807-812.
The Suzuki coupling with a protected L-tyrosine triflate, catalyzed by Tetrakis(triphenylphosphine)palladium(0), 10548, occurred in high yield without racemization when anhydrous K2CO3 in toluene was used as the base: J. Org. Chem., 57, 379 (1992). For Ni-catalyzed coupling with allylamines, see: J. Chem. Soc., Perkin 1, 2083 (1995). See Appendix 5.
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P280a-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.