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Ligand‐Controlled Palladium‐Catalyzed Carbonylation of Alkynols: Highly Selective Synthesis of α‐Methylene‐β‐Lactones
Author(s) -
Ge Yao,
Ye Fei,
Liu Jiawang,
Yang Ji,
Spannenberg Anke,
Jiao Haijun,
Jackstell Ralf,
Beller Matthias
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202006550
Subject(s) - carbonylation , chemistry , palladium , methylene , catalysis , ligand (biochemistry) , regioselectivity , phosphine , steric effects , combinatorial chemistry , imidazole , organic chemistry , carbon monoxide , receptor , biochemistry
The first general and regioselective Pd‐catalyzed cyclocarbonylation to give α‐methylene‐β‐lactones is reported. Key to the success for this process is the use of a specific sterically demanding phosphine ligand based on N ‐arylated imidazole ( L11 ) in the presence of Pd(MeCN) 2 Cl 2 as pre‐catalyst. A variety of easily available alkynols provide under additive‐free conditions the corresponding α‐methylene‐β‐lactones in moderate to good yields with excellent regio‐ and diastereoselectivity. The applicability of this novel methodology is showcased by the direct carbonylation of biologically active molecules including natural products.