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Photochemical Nozaki-Hiyama-Kishi Coupling Enabled by Excited Hantzsch Ester.

Yonghong LiuShuangjie LinDandan ZhangBingkun SongYunhe JinErjun HaoLei Shi
Published in: Organic letters (2022)
This work reports the first photochemical Nozaki-Hiyama-Kishi coupling enabled by bioinspired Hantzsch ester. The salient feature of this process is that commercially available and low-cost organic photoactive Hantzsch ester can serve as both an electron and a proton donor to reduce Cr/Ni to low-valent species and hydrolyze the Cr III -alkoxy bond, thus bypassing the use of stoichiometric metallic reductants and additives such as TMSCl and Cp 2 ZrCl 2 . The mild conditions and operationally easy method showed broad compatibility with various alkenyl triflates and aldehydes, including electron-poor pentafluorobenzaldehyde which failed under previous conditions.
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