Copper‐Catalyzed Aerobic Oxidative Transformation of Ketone‐Derived N‐Tosyl Hydrazones: An Entry to Alkynes1. Issue 52 (25th November 2014)

• Record Type: Journal Article
• Authors: Li, Xianwei; Liu, Xiaohang; Chen, Huoji; Wu, Wanqing; Qi, Chaorong; Jiang, Huanfeng
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 52(2014)
• Page Start: 14485
• Page End: 14489
• Publication Date: 2014-11-25
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201405058
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A novel strategy involving Cu‐catalyzed oxidative transformation of ketone‐derived hydrazone moiety to various synthetic valuable internal alkynes and diynes has been developed. This method features inexpensive metal catalyst, green oxidant, good functional group tolerance, high regioselectivity and readily available starting materials. Oxidative deprotonation reactions were carried out to form internal alkynes and symmetrical diynes. Cross‐coupling reactions of hydrazones with halides and terminal alkynes were performed to afford functionalized alkynes and unsymmetrical conjugated diynes. A mechanism proceeding through a Cu‐carbene intermediate is proposed for the CC triple bond formation.</p> </abstract>