Cadmium iodide mediated allenylation of terminal alkynes for the synthesis of methyl-substituted allenes

Xinjun Tang; Yulin Han; Shengming Ma

doi:10.1021/acs.orglett.5b00105

Cadmium iodide mediated allenylation of terminal alkynes for the synthesis of methyl-substituted allenes

Org Lett. 2015 Mar 6;17(5):1176-9. doi: 10.1021/acs.orglett.5b00105. Epub 2015 Feb 12.

Authors

Xinjun Tang¹, Yulin Han, Shengming Ma

Affiliation

¹ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, P. R. China.

PMID: 25674810
DOI: 10.1021/acs.orglett.5b00105

Abstract

A cadmium iodide mediated tandem reaction involving amine and two molecules of terminal alkynes for the synthesis of trisubstituted allenes has been developed. By applying this protocol, methyl-substituted allenes may be obtained easily from two molecules of terminal alkynes and pyrrolidine via methyl ketoniminium and propargylic amine formation, 1,5-hydride transfer and β-elimination.