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Conversion of 3,3,3-Trisubstituted Prop-1-ynes with tert-Butylhydrazine into 3,3,3-Trisubstituted Propionitriles Catalyzed by TpRh(C2H4)2/P(2-furyl)3

Yoshiya Fukumoto*, Yuto Tamura, Yasuaki Iyori and Naoto Chatani

*Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan, Email: fukumotochem.eng.osaka-u.ac.jp

Y. Fukumoto, Y. Tamura, Y. Iyori, N. Chatani, J. Org. Chem., 2016, 81, 3161-3167.

DOI: 10.1021/acs.joc.6b00116


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Abstract

The combination of TpRh(C2H4)2 and P(2-furyl)3 catalyzes the reaction of tertiary alkyl-substituted alkynes with tert-butylhydrazine providing 3,3,3-trisubstituted propionitrile derivatives. This reaction system is also applicable to 1,1-disubstituted propargyl alcohols and amines to afford the corresponding β-cyanohydrins and β-amino nitriles, respectively.

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Key Words

nitriles


ID: J42-Y2016