Rh(III)-Catalyzed Alkylation of 8-Methylquinolines with Oxabenzonorbornadienes
Sarthi1,2, Rohit Kumar1,2, Tamanna Sharma1
1C-H Activation & Phytochemistry Lab, Chemical Technology Division, CSIR-IHBT, Palampur 176061, India.
Abstract:
Herein, a concise Rh(III)-catalyzed C(sp3)-H alkylation of 8-methylquinolines with oxabenzonorbornadiene scaffolds and other strained olefins has been disclosed. The retention of the oxabenzonorbornadiene skeleton, broad substrate scope, and wide-ranging functional group tolerance are the key features of the developed catalytic methodology. Mechanistic studies revealed that the reaction does not involve a radical pathway, and the five-membered rhodacycle is the key intermediate. This is the first report on the C(sp3)-H alkylation of 8-methylquinolines with strained oxabenzonorbornadiene scaffolds (with ring retention).
Related Concept Videos
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Oxidation of Phenols to Quinones
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
Nucleophilic Aromatic Substitution: Elimination–Addition
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...


