Photodecarboxylative benzylations of phthalimides

Hatoum, Fadi, Gallagher, Sonia, Baragwanath, Louise, Lex, Johann, and Oelgemöller, Michael (2009) Photodecarboxylative benzylations of phthalimides. Tetrahedron Letters, 50 (46). pp. 6335-6338.

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Photoadditions of phenylacetates to phthalimides give the corresponding benzylated hydroxyphthalimidines in moderate to high yields of 29–90%. With 2-phenylpropanoate, photoaddition affords a diastereoisomeric mixture in a de of 24% in favour of the like-diastereoisomer. L-3-Phenyl lactate and 2-oxo-3-phenylpropanoate both furnish the benzylated product through subsequent loss of formaldehyde and decarbonylation, respectively.

Item ID: 10222
Item Type: Article (Research - C1)
ISSN: 1873-3581
Keywords: photodecarboxylation; benzylation; phthalimides; photochemistry; photoinduced electron transfer
Date Deposited: 12 Apr 2010 23:57
FoR Codes: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 100%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
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