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Tandem dual C(sp3)-H/C(sp2)-H functionalization: a radical cyclization of 2-isocyanobiphenyl with ether to 6-alkylated phenanthridine

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Abstract

A simple and efficient radical coupling of 2-isocyanobiphenyl with ethers was developed, providing a variety of 6-alkylated phenanthridines. Both cyclic and acyclic ethers are suitable substrates for this transformation, which comprised the functionalization of two C-H bonds: the sp3 C-H of ether and sp2 C-H of phenyl group. The kinetic isotope effect (KIE) revealed that the cleavage of sp3 C-H bond would be involved in the rate-determining step.

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Correspondence to Zhu ChengJian.

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Dedicated to Professor Qian Changtao on the occasion of his 80th birthday.

ZHU ChengJian was born in Henan, China, in 1966. He obtained his Ph. D. from Shanghai Institute of Organic Chemistry (CAS) in 1996 under the supervision of Professor Changtao Qian. Then he worked as a postdoctoral fellow successively in Universite de Bourgogne, University of Oklahoma, and then University of Houston from 1997 to 2000. He joined Nanjing University as an associate professor in 2000. Since 2003, he has been a professor at Nanjing University. His present research interests lie in organometallic chemistry and asymmetric catalysi

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Pan, C., Han, J. & ChengJian, Z. Tandem dual C(sp3)-H/C(sp2)-H functionalization: a radical cyclization of 2-isocyanobiphenyl with ether to 6-alkylated phenanthridine. Sci. China Chem. 57, 1172–1175 (2014). https://doi.org/10.1007/s11426-014-5118-7

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