Synthesis 2017; 49(16): 3662-3669
DOI: 10.1055/s-0036-1589032
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Oxidation-Hydroxylation and Oxidation-Methoxylation­ of N-Boc Indoles for the Synthesis of 3-Oxoindolines

Xiao-Yu Zhou*
a   Department of Chemistry and Chemical Engineering, Liupanshui Normal University, Liupanshui, 553004, P. R. of China   eMail: zhouxiaoyu20062006@126.com
,
Xia Chen*
a   Department of Chemistry and Chemical Engineering, Liupanshui Normal University, Liupanshui, 553004, P. R. of China   eMail: zhouxiaoyu20062006@126.com
,
Liang-Guang Wang
b   College of Chemistry and Chemical Engineering, Anshun University, Anshun, 561000, P. R. of China
,
Dan Yang
a   Department of Chemistry and Chemical Engineering, Liupanshui Normal University, Liupanshui, 553004, P. R. of China   eMail: zhouxiaoyu20062006@126.com
,
Zhi Li
a   Department of Chemistry and Chemical Engineering, Liupanshui Normal University, Liupanshui, 553004, P. R. of China   eMail: zhouxiaoyu20062006@126.com
› Institutsangaben
This work was supported by the Union Foundation of Science and Technology Department of Guizhou Province (Grant No. qiankehe LH zi [2015] number 7614) and the High-Level Talents Start-up Foundation of Liupanshui Normal University (Grant No. LPSSYKYJJ201501).
Weitere Informationen

Publikationsverlauf

Received: 22. Februar 2017

Accepted after revision: 20. April 2014

Publikationsdatum:
18. Mai 2017 (online)


Abstract

The palladium-catalyzed oxidation-hydroxylation and oxidation-methoxylation of N-Boc indoles for the synthesis of tert-butyl 2-hydroxy(methoxy)-3-oxoindoline-1-carboxylates and their derivatives is developed. The process occurs readily using PdCl2 as the catalyst and acetonitrile as the solvent to afford 3-oxoindolines in moderate to high yields. A mechanism for this Pd-catalyzed oxidation-hydroxylation and oxidation-methoxylation of N-Boc indoles is proposed.

Supporting Information

 
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