Palladium‐Catalyzed Cycloisomerization of (Z)‐1‐Iodo‐1, 6‐dienes to 3‐Aza‐bicyclo[4.1.0]hept‐2‐enes. Issue 6 (4th April 2019)

• Record Type: Journal Article
• Authors: Chi, Xiaochen; Meng, Long; Sun, Xi; Liu, Qing; Ai, Bing; Chen, Lei; Zhang, Daopeng; Zhao, Pingping; Dong, Yunhui; Liu, Hui
• Is Part Of: Asian journal of organic chemistry. Volume 8:Issue 6(2019)
• Page Start: 840
• Page End: 843
• Publication Date: 2019-04-04
• Subjects: Cycloisomerization -- Palladium-Catalyzed -- (Z)-1-Iodo-1, 6-diene -- 3-Aza-bicyclo[4.1.0]hept-2-ene -- Cascade reaction; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201900079
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: A Pd‐catalyzed cycloisomerization of ( Z )‐1‐iodo‐1, 6‐dienes was developed to construct 3‐aza‐bicyclo[4.1.0]hept‐2‐enes bearing substitutions at C1/C5. A wide array of ( Z )‐1‐iodo‐1, 6‐dienes could be converted to the desired compounds efficiently. On the basis of mechanistic studies, two pathways were proposed, in which compound alkyl iodide derivatives formed by reductive elimination of C sp 3 −Pd−I was proved to be a possible intermediate. Abstract : 1, 6‐dienes are very attractive and unique platform for the synthesis of various types of cyclic compounds. Herein, a Pd‐catalyzed cycloisomerization of ( Z )‐1‐iodo‐1, 6‐dienes has been developed to construct 3‐aza‐bicyclo[4.1.0]hept‐2‐enes bearing substitutions at C1/C5.