Journal
ORGANIC LETTERS
Volume 18, Issue 21, Pages 5496-5499Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b02698
Keywords
-
Categories
Funding
- SERB, New Delhi [SB/S1/OC-56/2013]
- Indian Institute of Science
- RL Fine Chem
- CSIR, New Delhi
Ask authors/readers for more resources
A novel mode of achieving site selectivity between C-2 and C-4 positions in the indole framework by altering the property of the ketone directing group is disclosed. Methyl ketone, as directing group, furnishes exclusively C-2 alkenylated product, whereas trifluoromethyl ketone changes the selectivity to C-4, indicating that the electronic nature of the directing group controls the unusual choice between a 5-membered and a 6-membered metallacycle. The screening of other carbonyl-derived directing groups reveals that strong and weak directing groups exhibit opposite selectivity. Experimental controls and deuteration experiments lend support to the proposed mechanism.
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