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Zhang XS, Zhang YF, Li ZW, et al. Synthesis of dibenzo[c,e]oxepin-5(7H)-ones from benzyl thioethers and carboxylic acids: rhodium-catalyzed double C-H activation controlled by different directing groups. Angew Chem Int Ed Engl. 2015;54(18):5478-82doi: 10.1002/anie.201500486.
Zhang, X. S., Zhang, Y. F., Li, Z. W., Luo, F. X., & Shi, Z. J. (2015). Synthesis of dibenzo[c,e]oxepin-5(7H)-ones from benzyl thioethers and carboxylic acids: rhodium-catalyzed double C-H activation controlled by different directing groups. Angewandte Chemie (International ed. in English), 54(18), 5478-82. https://doi.org/10.1002/anie.201500486
Zhang, Xi-Sha, et al. "Synthesis of dibenzo[c,e]oxepin-5(7H)-ones from benzyl thioethers and carboxylic acids: rhodium-catalyzed double C-H activation controlled by different directing groups." Angewandte Chemie (International ed. in English) vol. 54,18 (2015): 5478-82. doi: https://doi.org/10.1002/anie.201500486
Zhang XS, Zhang YF, Li ZW, Luo FX, Shi ZJ. Synthesis of dibenzo[c,e]oxepin-5(7H)-ones from benzyl thioethers and carboxylic acids: rhodium-catalyzed double C-H activation controlled by different directing groups. Angew Chem Int Ed Engl. 2015 Apr 27;54(18):5478-82. doi: 10.1002/anie.201500486. Epub 2015 Mar 10. PMID: 25757707.
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Angew Chem Int Ed Engl. 2015 Apr 27;54(18):5478-82. doi: 10.1002/anie.201500486. Epub 2015 Mar 10.

Synthesis of dibenzo[c,e]oxepin-5(7H)-ones from benzyl thioethers and carboxylic acids: rhodium-catalyzed double C-H activation controlled by different directing groups.

Angewandte Chemie (International ed. in English)

Xi-Sha Zhang, Yun-Fei Zhang, Zhao-Wei Li, Fei-Xian Luo, Zhang-Jie Shi

Affiliations

  1. Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering and Green Chemistry Center, Peking University, Beijing, 100871 (China).

PMID: 25757707 DOI: 10.1002/anie.201500486

Abstract

A rhodium(III)-catalyzed cross-coupling of benzyl thioethers and aryl carboxylic acids through the two directing groups is reported. Useful structures with diverse substituents were efficiently synthesized in one step with the cleavage of four bonds (CH, CS, OH) and the formation of two bonds (CC, CO). The formed structure is the privileged core in natural products and bioactive molecules. This work highlights the power of using two different directing groups to enhance the selectivity of a double CH activation, the first of such examples in cross-oxidative coupling.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: CH activation; carboxylic acids; cross-coupling; rhodium; synthetic methods

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