Platinum-Catalyzed Cascade Rearrangement Reaction of 1,5-Diynyl Esters: Unusual Regioselective 1,5-Hydride Migration.
A highly regioselective sequential 1,3-acyloxy migration/pentannulation/1,5-hydride migration reaction is disclosed which provides an efficient access to (E)-2-vinyl-3-oxo-1-methyleneindenes under neutral and mild reaction conditions. The migrated hydrogen atom was derived from an unactivated alkyl group, and the long-range 1,5-H shift was confirmed through related deuterium experiments.
Key Laboratory of Functional Small Organic Molecules, Ministry of Education, College of Chemistry&Chemical Engineering, Jiangxi Normal University, Ziyang Road 99, Nanchang, Jiangxi, 330022, P. R. China.
Hui
H
Zhu
Key Laboratory of Functional Small Organic Molecules, Ministry of Education, College of Chemistry&Chemical Engineering, Jiangxi Normal University, Ziyang Road 99, Nanchang, Jiangxi, 330022, P. R. China.
Jiapian
J
Huang
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang, Jiangxi, 330013, P. R. China).
Congbin
C
Fan
Key Laboratory of Functional Small Organic Molecules, Ministry of Education, College of Chemistry&Chemical Engineering, Jiangxi Normal University, Ziyang Road 99, Nanchang, Jiangxi, 330022, P. R. China. zchen@jxnu.edu.cn.
Zhiyuan
Z
Chen
D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry*; D007189:Indans / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D010984:Platinum / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D004952:Esters; D007189:Indans; D014753:Vinyl Compounds; D010984:Platinum; D006859:Hydrogen
1,5-diynyl esters; 1,5-hydride migration; platinum catalysis; rearrangements; regioselective