Ru- and Pd-Catalysed Synthesis of 2-Arylfurans by One-Flask Heck Arylation/Oxidation

被引:32
作者
Schmidt, Bernd [1 ]
Geissler, Diana [1 ]
机构
[1] Univ Potsdam, Inst Chem Organ Synthesechem, D-14476 Golm, Germany
关键词
Diazonium salts; Palladium; C-C coupling; Heck coupling; Furans; Oxidation; Oxygen heterocycles; RING-CLOSING METATHESIS; CYCLIC ENOL ETHERS; TANDEM CATALYSIS; DIAZONIUM SALTS; O-HETEROCYCLES; RUTHENIUM; INHIBITION; CYCLOADDITIONS; DERIVATIVES; REACTIVITY;
D O I
10.1002/ejoc.201100549
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2,5-Disubstituted furans were synthesized by one-flask Heck arylation/oxidation sequences. The starting materials are 2-substituted 2,3-dihydrofurans, conveniently available by RCM/isomerization sequences, and arenediazonium salts. These react in ligand-free Heck reactions to afford 2,5-disub-stituted 2,5-dihydrofurans, which are oxidized to the corresponding furans without isolation or intermediate workup. The oxidation is conveniently achieved with chloranil or DDQ, depending on the substrate.
引用
收藏
页码:4814 / 4822
页数:9
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