Photodecarboxylative benzylations of phthalimide in pH 7 buffer: a simple access to 3-arylmethyleneisoindolin-1-ones

Belluau, Vincent, Noeureuil, Pierre, Ratzke, Elfrun, Skvortsov, Aleksei, Gallagher, Sonia, Motti, Cherie Ann, and Oelgemöller, Michael (2010) Photodecarboxylative benzylations of phthalimide in pH 7 buffer: a simple access to 3-arylmethyleneisoindolin-1-ones. Tetrahedron Letters, 51 (36). pp. 4738-4741.

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Abstract

Photoadditions of phenylacetates to phthalimide in pH 7 buffer solution give the corresponding benzylated-hydroxyphthalimidines in moderate to high yields of up to 94%. In a micro-structured reactor, higher conversions and purities are achieved. With branched phenylacetates, photoaddition affords diastereoisomeric mixtures with low to moderate de values. Subsequent acid-catalyzed dehydration furnishes the corresponding 3-arylmethyleneisoindolin-1-ones in good to excellent yields and with high E-selectivities. Irradiation of the parent 3-phenylmethyleneisoindolin-1-one under oxidative conditions only leads to cis/trans-isomerization.

Item ID: 16790
Item Type: Article (Research - C1)
ISSN: 1873-3581
Keywords: photodecarboxylation; benzylation; phthalimide; photochemistry; micro-photochemistry; isoindolinones
Date Deposited: 05 May 2011 09:59
FoR Codes: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 50%
03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030505 Physical Organic Chemistry @ 30%
03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030501 Free Radical Chemistry @ 20%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
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