Catalyst- and additive-free Baeyer–Villiger-type oxidation of α-iodocyclopentenones to α-pyrones: using air as the oxidant

An efficient synthetic approach for the synthesis of α-pyrones via Baeyer–Villiger-type oxidation of α-iodocyclopentenones through a catalyst- and additive-free system using air as an environmentally benign oxidant is described. The reaction exhibits excellent functional group compatibility and provides a simple and efficient protocol for the construction of highly functionalized α-pyrones under mild reaction conditions.

Catalyst- and additive-free Baeyer–Villiger-type oxidation of α-iodocyclopentenones to α-pyrones: using air as the oxidant†

Yuanyuan Zhou,^a   Xianxiao Chen,^a   Xiangxiang Ling^a  and  Weidong Rao  *^a  

 Author affiliations

*Corresponding authors

^aJiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China
E-mail:weidong@njfu.edu.cn

6-Cyclohexyl-4-phenyl-2H-pyran-2-one (2e)[S3]

Product 2e was obtained as a pale-yellow solid in 68% yield (52 mg) following the general procedure, mp 96-97 °C;

1H NMR (600 MHz, CDCl3) δ 7.58-7.56 (m, 2H), 7.48-7.46 (m, 3H), 6.34 (d, J = 1.3 Hz, 1H), 6.26 (d, J = 0.8 Hz, 1H), 2.48 (tt, J = 11.8, 3.3 Hz, 1H), 2.04-2.01 (m, 2H), 1.87-1.84 (m, 2H), 1.47 (qd, J = 12.5, 3.0 Hz, 2H), 1.39-1.32 (m, 2H), 1.28-1.23 (m, 2H);

13C NMR (150 MHz, CDCl3) δ 169.8, 163.6, 155.6, 136.2, 130.5, 129.1, 126.7, 108.4, 100.9, 42.5, 30.6, 25.9, 25.8

http://www.rsc.org/suppdata/c9/gc/c9gc02725d/c9gc02725d1.pdf

 

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