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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