Photoinduced electron transfer cyclizations of aryl-linked phthalimides
Lee, Yong-Jun, Ahn, Do-Hwan, Lee, Kyoung-Sub, Kim, Ae Rhan, Yoo, Dong Jin, and Oelgemöller, Michael (2011) Photoinduced electron transfer cyclizations of aryl-linked phthalimides. Tetrahedron Letters, 52 (39). pp. 5029-5031.
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The photochemistry of arene-linked phthalimides incorporating the carboxylate or thioether donor group was investigated. Simple N-phthalimidophenyl alkanoates exclusively gave photoreduction (CO2H/H-exchange) products. In contrast, ω-phthalimido-meta-phenoxy carboxylates underwent photodecarboxylative cyclizations in yields of 6–48%. Likewise, catechol-linked derivatives furnished analogue cyclization products in 18–38% yield. Using the photodecarboxylation protocol, macrocyclic target compounds with ring sizes up to 17 could thus be realized. Two model phthalimides containing a thioether branch at the ortho-position of the arene-linker gave the analogue seven-membered cyclization products in yields of 28% and 35%, respectively.
|Item Type:||Article (Refereed Research - C1)|
|Keywords:||photodecarboxylation; phthalimide; photoinduced electron transfer; photochemistry; photocyclization|
|FoR Codes:||03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 50%|
03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030505 Physical Organic Chemistry @ 50%
|SEO Codes:||97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%|
|Deposited On:||29 Sep 2011 13:51|
|Last Modified:||18 Oct 2013 01:20|
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