A convenient and efficient C–OH bond activation, PdCl2(PPh3)2 catalyzed, C–C bond formation of tautomerizable quinolinones with the aid of BOP reagent and boronic acids

Yadavalli Suneel Kumar; C. Dasaradhan; Kamalakannan Prabakaran; Fazlur-Rahman Nawaz Khan; Euh Duck Jeong; Eun Hyuk Chung; Hyun Gyu Kim

doi:10.1039/C4RA05161K

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A convenient and efficient C–OH bond activation, PdCl₂(PPh₃)₂ catalyzed, C–C bond formation of tautomerizable quinolinones with the aid of BOP reagent and boronic acids†

Yadavalli Suneel Kumar,^a C. Dasaradhan,^a Kamalakannan Prabakaran,^a Fazlur-Rahman Nawaz Khan,*^ab Euh Duck Jeong,*^b Eun Hyuk Chung^b and Hyun Gyu Kim^b

Author affiliations

* Corresponding authors

^a Organic and Medicinal Chemistry Research Laboratory, Organic Chemistry Division, School of Advanced Sciences, VIT-University, Vellore 632 014, Tamil Nadu, India
E-mail: nawaz_f@yahoo.co.in, fnkn@kbsi.re.kr

^b Korea Basic Science Institute, Busan Center, Busan 618 230, South Korea
E-mail: edjeong@kbsi.re.kr

Abstract

An efficient, highly chemoselective PdCl₂(PPh₃)₂ catalyzed, C–C bond formation of tautomerizable quinolinones with various boronic acids via C–OH bond activation using benzotriazol-1-yloxytris(dimethylamino) phosphonium hexafluorophosphate (BOP) reagent in the presence of K₂CO₃/1,4-dioxane system under aqueous condition, leads to the formation of functionalized quinolines in excellent yields, which offers great utility advantages in the synthesis of interesting compounds.

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Article information

DOI: https://doi.org/10.1039/C4RA05161K
Article type: Paper
Submitted: 31 May 2014
Accepted: 06 Aug 2014
First published: 12 Aug 2014

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RSC Adv., 2014,4, 40259-40268

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A convenient and efficient C–OH bond activation, PdCl₂(PPh₃)₂ catalyzed, C–C bond formation of tautomerizable quinolinones with the aid of BOP reagent and boronic acids

Y. S. Kumar, C. Dasaradhan, K. Prabakaran, F. Nawaz Khan, E. D. Jeong, E. H. Chung and Hyun Gyu Kim, RSC Adv., 2014, 4, 40259 DOI: 10.1039/C4RA05161K

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