Iridium-Catalyzed Direct Regioselective C4-Amidation of Indoles under Mild Conditions
Shuyou Chen1, Boya Feng1, Xuesong Zheng1
1Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University , 29 Wangjiang Road, Chengdu 610064, P. R. China.
Abstract:
An efficient Ir-catalyzed amidation of indoles with sulfonyl azides is disclosed, affording diverse C4-amidated indoles exclusively under mild conditions. In this protocol, a variety of indoles with commonly occurring functional groups such as formyl, acetyl, carboxyl, amide, and ester at the C3 position are well tolerated.
More Related Videos
09:54Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
Related Concept Videos
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
