Photoarylation of alkenes and heteroaromatics by dibromo-BINOLs in aqueous solution.
The photochemistry of 6,6'-dibromo-BINOL (BINOL = 2,2'-dihydroxy-1,1'-binaphthyl) under mild basic conditions and its methyl and triisopropylsilyl ethers has been investigated in neat and aqueous acetonitrile through product distribution analysis and laser flash photolysis. Arylation and alkylation have been successfully achieved in the presence of allyltrimethylsilane, ethyl vinyl ether, pyrrole, pyridine, thiophene, benzene, and indole. Such a photoreactivity offers a metal and protecting group free synthetic protocol toward mono- and disubstituted 6-aryl/alkyl BINOLs, since the BINOL chirality is preserved in the photoactivation process.
Verga
Daniela
D
Dipartimento di Chimica Organica, Università di Pavia, V.le Taramelli 10, 27100 Pavia, Italy.
Doria
Filippo
F
Pretali
Luca
L
Freccero
Mauro
M
D000475:Alkenes / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D015394:Molecular Structure; D009284:Naphthols / Q000138:chemical synthesis* / Q000737:chemistry*; D010777:Photochemistry; D012996:Solutions; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
D000475:Alkenes; D006571:Heterocyclic Compounds; D006841:Hydrocarbons, Aromatic; D009284:Naphthols; D012996:Solutions; D014867:Water