Abstract
The past decades have witnessed the fast growth of ortho-directing group assisted in CH activation and olefination. Herein we addressed these olefination products’ photo-induced E → Z isomerization in term of various ortho-substitution groups. Initially, we discovered ortho benzoxazolyl aryl acrylates effectively undertook E → Z isomerization (up to 88% yields) under 365 nm direct irradiation. Furthermore, scoping other five directing groups in CH activation and olefination revealed that acetylamino group also present to be good ortho-substituted groups that enhancing E → Z isomerization. Controlled experiment shows the substitution position is vital for photo-induced isomerization or [2 + 2] cycloaddition. Lastly, prevalent interesting fluorescent quenching/change phenomenon were always in accompany with the isomerization. X-ray single crystallography disclose the isomerization process undertook significant conjugated distortion of the aryl acrylates fragment, we proposed such change could contribute to fluorescent and absorbent decrease.
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