Journal
CHEMICAL COMMUNICATIONS
Volume 58, Issue 94, Pages 13151-13154Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2cc04772a
Keywords
-
Categories
Funding
- CSIR, New Delhi [MLP0159]
- UGC, New Delhi [CRG/2021/000878]
- INSPIRE Research Fellowship
Ask authors/readers for more resources
The Rh(iii)-catalysed C(sp(3))-H bond amidation of 8-methylquinolines using N-hydroxyphthalimides as the amidation source is explored. Diversely substituted 8-methylquinolines were well tolerated and furnished the amidated products in excellent yields with high regioselectivity. The developed reaction conditions were also applied successfully for the secondary C(sp(3))-H amidation of 8-ethylquinolines, showing its applicability in gram-scale synthesis and product diversification.
Herein, the Rh(iii)-catalysed C(sp(3))-H bond amidation of 8-methylquinolines using N-hydroxyphthalimides as the amidation source is explored. Diversely substituted 8-methylquinolines were well tolerated and furnished the amidated products in excellent yields with high regioselectivity. The developed reaction conditions were also applied successfully for the secondary C(sp(3))-H amidation of 8-ethylquinolines. Besides that, the reaction is also applicable for the gram-scale synthesis of the amidated product. In addition, the late-stage amidation of santonin oxime as well as carvone oxime and the diversification of the amidated product was also carried out to illustrate the relevance of the developed methodology. Mechanistic studies revealed that the current reaction proceeds through a five-membered rhodacycle intermediate and does not involve the radical pathway.
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