Synthesis 2020; 52(05): 703-710
DOI: 10.1055/s-0039-1690245
paper
© Georg Thieme Verlag Stuttgart · New York

Hydroalkylation of Unactivated Alkenes with Ketones and 5-Benzylfurfurals Enabled by Amine/Pd(II) Cooperative Catalysis

Mostafa Sayed
a  Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China   Email: gonglz@ustc.edu.cn
b  Department of Chemistry, Faculty of Science, New Valley University, El-Kharja 72511, Egypt
,
Hong-Cheng Shen
a  Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China   Email: gonglz@ustc.edu.cn
,
Ling Zhang
a  Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China   Email: gonglz@ustc.edu.cn
,
Liu-Zhu Gong
a  Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China   Email: gonglz@ustc.edu.cn
c  Center for Excellence in Molecular Synthesis of CAS, Hefei 230026, P. R. of China
› Author Affiliations
We are grateful for financial support from National Natural Science Foundation of China (21831007) and for a CAS-TWAS Fellowship.
Further Information

Publication History

Received: 05 September 2019

Accepted after revision: 21 October 2019

Publication Date:
13 November 2019 (online)


§ M. Sayed and H.-C. Shen contributed equally to this manuscript

Abstract

An intermolecular addition of ketones to unactivated alkenes has been developed by means of Pd(II)/amine cooperative catalysis, which incorporates the simultaneous activation of amide-containing alkenes and α-carbon of ketones enabled by Pd(II) catalyst and enamine, respectively. Moreover, the addition of 5-benzylfurfural derivatives to an unactivated alkene has also been achieved by integrating Pd(II) and trienamine catalysis to provide γ-adducts at the benzylic position of furfurals in good to high yields.

Supporting Information

 
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