Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 15, Pages 8509-8521Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01098
Keywords
-
Categories
Funding
- National Natural Science Foundation of China (NSFC) [21572047]
- Program for Innovative Research Team in Science and Technology in Universities of Henan Province [15IRTSTHN003]
- Program for Science and Technology Innovation Talents in Universities of Henan Province [15HASTIT005]
- Plan for Scientific Innovation Talents of Henan Province [184200510012]
Ask authors/readers for more resources
In this paper, a novel and efficient synthesis of 2-alkenylindoles and 2-alkenylindole-3-carboxylates via the cascade reactions of N-nitrosoanilines with propargyl alcohols is presented. Mechanistically, the formation of the title compounds is triggered by a Rh(III)-catalyzed C(sp(2))-H alkenylation of N-nitrosoaniline with propargyl alcohol followed by the simultaneous intramolecular amination/cyclization, NO extrusion, and dehydration. With this method, a variety of diversely substituted 2-alkenylindole derivatives were prepared in good efficiency and exclusive site-selectivity. To the best of our knowledge, this is the first example in which the indoyl and the alkenyl units are formed sequentially in one pot from halide-free substrates through a redox neutral C-H bond activation. In addition, the utility of the 2-alkenylindole products thus obtained was remarkably showcased by their facile transformations into synthetically and biologically significant compounds such as 2-acylindole, benzocarbazole, indoloquinoline, pyridoindolone, cyclopentaindolone, and indenoindolone.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available