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Sequentially Pd/Cu‐Catalyzed Alkynylation‐Oxidation Synthesis of 1,2‐Diketones and Consecutive One‐Pot Generation of Quinoxalines
Author(s) -
Niesobski Patrik,
Martínez Ivette Santana,
Kustosz Sebastian,
Müller Thomas J. J.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900783
Subject(s) - chemistry , catalysis , one pot synthesis , aryl , alkyne , alkynylation , combinatorial chemistry , sonogashira coupling , palladium , organic chemistry , halide , medicinal chemistry , alkyl
We report a simple and efficient one‐pot synthesis of 1,2‐diketones by concatenation of two Pd/Cu‐catalyzed processes: Pd 0 /Cu I ‐catalyzed Sonogashira coupling of terminal alkynes with aryl (pseudo)halides furnishes internal alkynes, which are directly transformed by Pd II /Cu II ‐catalyzed Wacker‐type oxidation with DMSO and oxygen as dual oxidants to furnish 1,2‐diketones. With this efficient, catalyst economical process, various aryl iodides and triflates are efficiently transformed in high yields into symmetrically and unsymmetrically substituted 1,2‐diketones with various functional groups. This process can be readily extended to a consecutive one‐pot synthesis of quinoxalines in a diversity‐oriented fashion.