Affiliation:
1. Green Catalysis Center, College of Chemistry Zhengzhou University 100 Kexue Road Zhengzhou Henan 450001 China
2. Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering Shanghai Jiao Tong University 800 Dongchuan Road Shanghai 200240 China
Abstract
Comprehensive SummarySkipped dienes are of great importance but remain challenging to synthesize because of the presence of a sp3 hybrid carbon between the two alkenes. Herein, we have developed the first nickel‐catalyzed regio‐, (E)‐stereo‐ and linear‐selective ring‐opening/cross‐coupling reaction of vinylaziridines with organoboronic acids under mild conditions to construct various skipped aminodienes. The reaction exhibits wide functional‐group compatibility, and could be adapted for the introduction of skipped aminodiene functionality into bioactive molecules. In addition, the reaction could be carried out on a gram‐scale, delivering the ring‐opening products in high yields and with linear‐selectivity (90% yield, l : b >20 : 1). Furthermore, DFT calculations and mechanistic experiments provided detailed insights into the mechanism.
Funder
National Key Research and Development Program of China
National Natural Science Foundation of China