Cross-Coupling Reactions of Monosubstituted Tetrazines

被引:11
|
作者
Hoff, Lukas, V [1 ]
Schnell, Simon D. [1 ]
Tomio, Andrea [1 ]
Linden, Anthony [1 ]
Gademann, Karl [1 ]
机构
[1] Univ Zurich, Dept Chem, CH-8057 Zurich, Switzerland
关键词
DIELS-ALDER REACTIONS; REDUCTIVE ELIMINATION; OXIDATIVE ADDITION; ARYL HALIDES; C-H; PALLADIUM;
D O I
10.1021/acs.orglett.1c01813
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Ag-mediated Pd-catalyzed cross-coupling method for 3-bromo-1,2,4,5-tetrazine with boronic acids is presented. Electronic modification of the 1,1'-bis(diphenylphosphine)ferrocene (dppf) ligand was found to be crucial for good turnover. Using this fast method, a variety of alkyl-, heteroatom-, and halide-substituted aryl-and heteroaryl-tetrazines were prepared (29 examples, up to 87% yield).
引用
收藏
页码:5689 / 5692
页数:4
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