19357-17-6Relevant academic research and scientific papers
Homobenzylic Oxygenation Enabled by Dual Organic Photoredox and Cobalt Catalysis
McManus, Joshua B.,Griffin, Jeremy D.,White, Alexander R.,Nicewicz, David A.
, p. 10325 - 10330 (2020)
Activation of aliphatic C(sp3)-H bonds in the presence of more activated benzylic C(sp3)-H bonds is often a nontrivial, if not impossible task. Herein we show that leveraging the reactivity of benzylic C(sp3)-H bonds to achieve reactivity at the homobenzylic position can be accomplished using dual organic photoredox/cobalt catalysis. Through a two-part catalytic system, alkyl arenes undergo dehydrogenation followed by an anti-Markovnikov Wacker-type oxidation to grant benzyl ketone products. This formal homobenzylic oxidation is accomplished with high atom economy without the use of directing groups, achieving valuable reactivity that traditionally would require multiple chemical transformations.
Photoinduced electron transfer cyclizations of aryl-linked phthalimides
Lee, Yong-Jun,Ahn, Do-Hwan,Lee, Kyoung-Sub,Kim, Ae Rhan,Yoo, Dong Jin,Oelgem?ller, Michael
experimental part, p. 5029 - 5031 (2011/10/09)
The photochemistry of arene-linked phthalimides incorporating the carboxylate or thioether donor group was investigated. Simple N-phthalimidophenyl alkanoates exclusively gave photoreduction (CO 2H/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.
