I2-Catalyzed Direct α-Hydroxylation of β ... - ACS Publications

Chun-Bao Miao*, Yan-Hong Wang, Meng-Lei Xing, Xin-Wei Lu, Xiao-Qiang Sun*, and Hai-Tao Yang. School of Petrochemical Engineering, Changzhou ...
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I2‑Catalyzed Direct α‑Hydroxylation of β‑Dicarbonyl Compounds with Atmospheric Oxygen under Photoirradiation Chun-Bao Miao,* Yan-Hong Wang, Meng-Lei Xing, Xin-Wei Lu, Xiao-Qiang Sun,* and Hai-Tao Yang School of Petrochemical Engineering, Changzhou University, Changzhou 213164, People’s Republic of China S Supporting Information *

ABSTRACT: An I2-catalyzed hydroxylation of β-dicarbonyl moieties using air as the oxidant under photoirradiation has been developed for the easy preparation of α-hydroxy-βdicarbonyl compounds. The transformation was completed with only 1 mol % of I2. With α-unsubstituted malonates, the hydroxylated dimerization product was afforded as the predominant product along with a minor product, α,αdihydroxyl malonate. tates to generate α-ketoesters as the major product accompanied by the formation of minor α-hydroxylation products (