title: Synthesis of 2-naphthols via carbonylative Stille coupling reaction of 2-bromobenzyl bromides with tributylallylstannane followed by the Heck reaction.
abstract: A method for the synthesis of 2-naphthols 4 is described. The carbonylative Stille coupling reactions of 2-bromobenzyl bromides with tributylallylstannane to produce 2-bromobenzyl β,γ-unsaturated ketones 2 in satisfactory to excellent yields has been achieved. The isomerization of 2-bromobenzyl β,γ-unsaturated ketones 2 can readily occur under basic conditions to generate 2-bromobenzyl α,β-unsaturated ketones 3. The 2-bromobenzyl α,β-unsaturated ketones 3 can be transformed into 2-naphthols 4 via intramolecular Heck reaction in satisfactory to good yields.
authors.affiliation: State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China.
authors.forename: Yao
authors.initials: Y
authors.lastname: Dai
authors.forename: Xiujuan
authors.initials: X
authors.lastname: Feng
authors.forename: Hesong
authors.initials: H
authors.lastname: Liu
authors.forename: Hua
authors.initials: H
authors.lastname: Jiang
authors.forename: Ming
authors.initials: M
authors.lastname: Bao
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis*; D002248:Carbon Monoxide / Q000737:chemistry; D002384:Catalysis; D007536:Isomerism; D007659:Ketones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009284:Naphthols / Q000138:chemical synthesis*; D017971:Tin Compounds / Q000737:chemistry*
chemical_list: D001688:Biological Products; D007659:Ketones; D009284:Naphthols; D017971:Tin Compounds; C031525:stannane; D002248:Carbon Monoxide