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American Chemical Society, Journal of Organic Chemistry, 10(75), p. 3477-3480, 2010

DOI: 10.1021/jo100349h

Wiley-VCH Verlag, ChemInform, 38(41), p. no-no, 2010

DOI: 10.1002/chin.201038098

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Photoarylation of Alkenes and Heteroaromatics by Dibromo-BINOLs in Aqueous Solution

Journal article published in 2010 by Daniela Verga ORCID, Filippo Doria, Luca Pretali, Mauro Freccero ORCID
This paper is available in a repository.
This paper is available in a repository.

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Abstract

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.