Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Photochemical Cleavage of Benzylic C–O Bond Facilitated by an Ortho or Meta Amino Group

Photochemical Cleavage of Benzylic C–O Bond Facilitated by an Ortho or Meta Amino Group
Pengfei Wang, Xiong Ding
The excited state meta effect, also known as the meta-ortho effect, results from selective electron transmission from an electron-donating group to the meta and ortho sites on an aromatic ring in its first excited singlet state. This effect facilitates photochemical cleavage of benzylic C–O or C–N bond to release the corresponding alcohol, carboxylic acid, or amine when an electron-donating amino group is at the meta position, as demonstrated in our recent work of using a 3-diethylaminobenzyl (DEABn) group as an effective photolabile protecting group (PPG). Herein, we demonstrate that an ortho amino group can also facilitate benzylic C–O bond cleavage to release an alcohol or carboxylic acid. However, an amino group at the meta position results in a PPG with better overall chemical and photochemical properties.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00927

DOI: 10.1021/acs.joc.7b00927

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