Domino Carbopalladation/CH Functionalization Sequence: An Expedient Synthesis of Bis‐Heteroaryls through Transient Alkyl/Vinyl–Palladium Species Capture. Issue 2 (2nd December 2015)

• Record Type: Journal Article
• Authors: Sharma, Upendra K.; Sharma, Nandini; Kumar, Yogesh; Singh, Brajendra K.; Van der Eycken, Erik V.
• Is Part Of: Chemistry. Volume 22:Issue 2(2016)
• Page Start: 481
• Page End: 485
• Publication Date: 2015-12-02
• Subjects: CH activation -- domino reactions -- heterocycles -- microwave chemistry -- palladium; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201503708
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A microwave‐assisted highly efficient intermolecular domino carbopalladation/CH functionalization sequence has been developed to access bis‐heteroaryl frameworks in a single operation. The reaction involves carbopalladation of the halogenated acrylamides or phenylpropiolamides by the Pd(0) catalysis, followed by the direct (hetero)arylation to give products with good to excellent yields. The synthetic utility of this method was also extended towards the application of the Ugi‐adduct as the starting material. Abstract : A selective method! Azoles have been used as nucleophiles to trap the σ‐alkyl/vinyl–palladium species for the synthesis of bis‐heteroaryl frameworks by a domino carbopalladation/CH functionalization strategy. This method exhibits remarkable selectivity, high functional group tolerance, and provides good to excellent product yields (see scheme).