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Rhodium-catalyzed oxidative cycloaddition of benzamides and alkynes via C-H/N-H activation.
J Am Chem Soc. 2010 Aug 04; 132(30):10565-9.JA

Abstract

The oxidative cycloaddition of benzamides and alkynes has been developed. The reaction utilizes Rh(III) catalysts in the presence of Cu(II) oxidants, and is proposed to proceed by N-H metalation of the amide followed by ortho C-H activation. The resultant rhodacycle undergoes alkyne insertion to form isoquinolones in good yield. The reaction is tolerant of extensive substitution on the amide, alkyne, and arene, including halides, silyl ethers, and unprotected aldehydes as substituents. Unsymmetrical alkynes proceed with excellent regioselectivity, and heteroaryl carboxamides are tolerated leading to intriguing scaffolds for medicinal chemistry. A series of competition experiments shed further light on the mechanism of the transformation and reasons for selectivity.

Authors+Show Affiliations

Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.No affiliation info available

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

20662529

Citation

Hyster, Todd K., and Tomislav Rovis. "Rhodium-catalyzed Oxidative Cycloaddition of Benzamides and Alkynes Via C-H/N-H Activation." Journal of the American Chemical Society, vol. 132, no. 30, 2010, pp. 10565-9.
Hyster TK, Rovis T. Rhodium-catalyzed oxidative cycloaddition of benzamides and alkynes via C-H/N-H activation. J Am Chem Soc. 2010;132(30):10565-9.
Hyster, T. K., & Rovis, T. (2010). Rhodium-catalyzed oxidative cycloaddition of benzamides and alkynes via C-H/N-H activation. Journal of the American Chemical Society, 132(30), 10565-9. https://doi.org/10.1021/ja103776u
Hyster TK, Rovis T. Rhodium-catalyzed Oxidative Cycloaddition of Benzamides and Alkynes Via C-H/N-H Activation. J Am Chem Soc. 2010 Aug 4;132(30):10565-9. PubMed PMID: 20662529.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium-catalyzed oxidative cycloaddition of benzamides and alkynes via C-H/N-H activation. AU - Hyster,Todd K, AU - Rovis,Tomislav, PY - 2010/7/29/entrez PY - 2010/7/29/pubmed PY - 2010/12/14/medline SP - 10565 EP - 9 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 132 IS - 30 N2 - The oxidative cycloaddition of benzamides and alkynes has been developed. The reaction utilizes Rh(III) catalysts in the presence of Cu(II) oxidants, and is proposed to proceed by N-H metalation of the amide followed by ortho C-H activation. The resultant rhodacycle undergoes alkyne insertion to form isoquinolones in good yield. The reaction is tolerant of extensive substitution on the amide, alkyne, and arene, including halides, silyl ethers, and unprotected aldehydes as substituents. Unsymmetrical alkynes proceed with excellent regioselectivity, and heteroaryl carboxamides are tolerated leading to intriguing scaffolds for medicinal chemistry. A series of competition experiments shed further light on the mechanism of the transformation and reasons for selectivity. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/20662529/Rhodium_catalyzed_oxidative_cycloaddition_of_benzamides_and_alkynes_via_C_H/N_H_activation_ L2 - https://doi.org/10.1021/ja103776u DB - PRIME DP - Unbound Medicine ER -
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