Photodecarboxylative additions of α-thioalkyl-substituted carboxylates to alkyl phenylglyoxylates

Tan, Su Bee, Shvydkiv, Oksana, Fiedler, Jana, Hatoum, Fadi, Nolan, Kieran, and Oelgemöller, Michael (2010) Photodecarboxylative additions of α-thioalkyl-substituted carboxylates to alkyl phenylglyoxylates. Synlett, 15. pp. 2240-2243.

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Abstract

Irradiations of alkyl phenylglyoxylates with sulfur-containing carboxylates yielded the corresponding photodecarboxylative addition products in moderate to good yields of 26-58%. Reductive photodimerization competed with decarboxylative addition in all cases. The reaction protocol was successfully transferred to a microreactor. With potassium 2-(methylsulfanyl)propionate, photoadditions gave diastereomeric mixtures with low selectivity for the like-isomer.

Item ID: 16789
Item Type: Article (Refereed Research - C1)
Keywords: photodecarboxylation; phenylglyoxolates; photochemistry; photoinduced electron transfer; microreactor
ISSN: 1437-2096
Date Deposited: 13 May 2011 04:04
FoR Codes: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 50%
03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030504 Organic Green Chemistry @ 25%
03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030505 Physical Organic Chemistry @ 25%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
Citation Count from Web of Science Web of Science 8
Downloads: Total: 3
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