Modular Synthesis of Unsymmetrical 1, 4‐Diamino‐2‐butynes by Cu–Catalyzed Sequential Decarboxylative A3‐Coupling/Petasis Reaction/A3‐Coupling. Issue 4 (19th February 2021)

• Record Type: Journal Article
• Authors: Zhu, Shuangyuan; Feng, Huangdi; Hu, Shengyun; Guo, Tingting; Li, Ming; Tan, Shaoying; Huang, Liliang; Huang, Junhai
• Is Part Of: Asian journal of organic chemistry. Volume 10:Issue 4(2021)
• Page Start: 816
• Page End: 819
• Publication Date: 2021-02-19
• Subjects: Copper -- Cross-coupling -- Propiolic acid -- 1, 4-Diamino-2-butynes; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202100026
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: 1, 4‐diamino‐2‐butynes are important structural motifs in biologically active molecules, however, their synthesis with high selectivity remains a challenge. Herein, we develop an effective and straightforward strategy for the modular synthesis of unsymmetrical 1, 4‐diamino‐2‐butynes with a high chemoselectivity. This transformation involves a cascade process of copper‐catalyzed decarboxylative A 3 ‐coupling, Petasis reaction, and A 3 ‐coupling, providing a rapid route for synthesizing various target products with broadly functional tolerance and up to 76% yield. Abstract : The Unsymmetric 1.4‐diamino‐2‐butynes structure was constructed by sequential decarboxylative A 3 ‐coupling/Petasis reaction/A 3 ‐coupling of five components under the catalysis of copper. 31 Examples were used to prove the high tolerance of the strategy.