Metal-Free Carbonyl-Assisted Regioselective Hydration of Alkynes: An Access to Dicarbonyls

• DOI: 10.1021/acs.orglett.9b01649
• Publication Date: 2019-06-14T14:48:48Z
• Authors: Shalini Verma; Manoj Kumar; Pawan K. Mishra; Akhilesh K. Verma
• Keywords: 01 natural sciences; 0104 chemical sciences

Metal-free regioselective hydration of o-alkynylaldehydes with the assistance of neighboring carbonyl oxygen is disclosed. The developed protocol provides a facile route to synthesize a series of multisubstituted carbonyl containing scaffolds that enable the potential application toward the synthesis of highly diversified 5-azaindoles. γ-Carbolines and 2,8-diazacarbazoles can also be accessed directly without isolating the dicarbonyl compounds. The developed methodology is operationally simple and environment-friendly, tolerates a wide variety of functional groups, and is applicable toward large scale synthesis.