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Palladium‐Catalyzed Regio‐ and Stereoselective Cross‐Addition of Terminal Alkynes to Ynol Ethers and Synthesis of 1,4‐Enyn‐3‐ones
Author(s) -
Hari Babu Madala,
Dwivedi Vikas,
Kant Ruchir,
Sridhar Reddy Maddi
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201411261
Subject(s) - catalysis , palladium , stereoselectivity , chemistry , enol , conjugated system , allylic rearrangement , combinatorial chemistry , ligand (biochemistry) , reaction conditions , organic chemistry , biochemistry , receptor , polymer
Abstract Conjugated enynes, enol ethers, and enynones are versatile building blocks that can be elaborated by a wide variety of synthetic transformations. The selective synthesis of such units is a prerequisite for their effective utilization. The synthesis of conjugated 2‐phenoxyenynes through a palladium‐catalyzed cross‐addition of terminal alkynes to phenylethynyl ethers (hydroalkynylation) is now presented. The reaction is highly regio‐, stereo‐, and chemoselective, and shows excellent tolerance toward functional groups. The addition further features very mild reaction conditions (room temperature) and an inexpensive catalytic system (without a ligand and with a cheaply available Pd catalyst). The thus synthesized enynyl ethers with allylic hydroxy tethers, which survived the reaction, were shown to be ready precursors for valuable 1‐en‐4‐yn‐3‐ones.