Mild and highly regioselective synthesis of biaryl acids via Rh(I)-catalyzed cross-dehydrogenative coupling of benzoic acids using sodium chlorite as oxidant

doi:10.1007/s11705-017-1693-4

Front. Chem. Sci. Eng.

2018, Vol. 12

Issue (1) : 3-8 https://doi.org/10.1007/s11705-017-1693-4

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Mild and highly regioselective synthesis of biaryl acids via Rh(I)-catalyzed cross-dehydrogenative coupling of benzoic acids using sodium chlorite as oxidant

Yun Liu^1,², Youquan Zhu¹, Chaojun Li¹(

)

¹. Department of Chemistry, FQRNT Center for Green Chemistry and Catalysis, McGill University, Montreal, Quebec, H3A0B8, Canada
². Department of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou 221116, China

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Abstract

A mild and efficient synthesis for the biaryl acids via rhodium-catalyzed cross-dehydrogenative coupling reaction has been developed. This novel protocol with sodium chlorite as an oxidant featured many advantages such as mild reaction conditions, high regioselectivity, tolerance of various functional groups, and good to excellent yields.

Keywords biaryl acids cross-dehydrogenative coupling rhodium-catalyzed

Corresponding Author(s): Chaojun Li

Just Accepted Date: 30 October 2017 Online First Date: 26 December 2017 Issue Date: 26 February 2018

Cite this article:

Yun Liu,Youquan Zhu,Chaojun Li. Mild and highly regioselective synthesis of biaryl acids via Rh(I)-catalyzed cross-dehydrogenative coupling of benzoic acids using sodium chlorite as oxidant[J]. Front. Chem. Sci. Eng., 2018, 12(1): 3-8.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-017-1693-4
https://academic.hep.com.cn/fcse/EN/Y2018/V12/I1/3

Fig.1 Scheme 1 Rhodium-catalyzed dimerization of benzoic acid

Tab.1 Optimization of reaction conditions ^a)

Fig.2

Tab.2 Substrate scope of benzoic acids^{a), b)}

Fig.5 Scheme 2 Comparison of the two catalytic systems

Fig.6 Scheme 3Plausible mechanism

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