Synthesis of 6,7-dihydro-5H-cyclopenta[b]pyridin-5-one analogues through manganese-catalyzed oxidation of the CH2 adjacent to pyridine moiety in water

Lanhui Ren; Lianyue Wang; Ying Lv; Sensen Shang; Bo Chen; Shuang Gao

doi:10.1039/C4GC02471K

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Synthesis of 6,7-dihydro-5H-cyclopenta[b]pyridin-5-one analogues through manganese-catalyzed oxidation of the CH₂ adjacent to pyridine moiety in water†

Lanhui Ren,^ab Lianyue Wang,^a Ying Lv,^a Sensen Shang,^ab Bo Chen^ab and Shuang Gao*^a

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* Corresponding authors

^a Dalian Institute of Chemical Physics, the Chinese Academy of Sciences and Dalian National Laboratory for Clean Energy, DNL, 457 Zhongshan Road, Dalian, P. R. China
E-mail: sgao@dicp.ac.cn
Fax: (+86) 0411-8437-9248

^b Graduate School of the Chinese Academy of Sciences, Beijing, P. R. China

Abstract

Direct oxidation of 2,3-cyclopentenopyridine analogues to 6,7-dihydro-5H-cyclopenta[b]pyridin-5-one analogues was achieved using Mn(OTf)₂ as a catalyst and t-BuOOH (65% in H₂O) as an oxidant at 25 °C in H₂O with high yield and excellent chemoselectivity for the first time. The catalytic system was also used efficiently for the direct oxidation of substituted benzylpyridines and 2-ethylpyridine in t-BuOH.

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Article information

DOI: https://doi.org/10.1039/C4GC02471K
Article type: Communication
Submitted: 18 Dec 2014
Accepted: 12 Feb 2015
First published: 12 Feb 2015

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Green Chem., 2015,17, 2369-2372

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Synthesis of 6,7-dihydro-5H-cyclopenta[b]pyridin-5-one analogues through manganese-catalyzed oxidation of the CH₂ adjacent to pyridine moiety in water

L. Ren, L. Wang, Y. Lv, S. Shang, B. Chen and S. Gao, Green Chem., 2015, 17, 2369 DOI: 10.1039/C4GC02471K

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