Palladium Catalyzed C-O Coupling of Amino Alcohols for the Synthesis of Aryl Ethers

被引:18
作者
Mikus, Malte S. [1 ]
Sanchez, Carina [1 ]
Fridrich, Cary [1 ,2 ]
Larrow, Jay F. [1 ]
机构
[1] Novartis Inst Biomed Res, Global Discovery Chem, 250 Massachusetts Ave, Cambridge, MA 02139 USA
[2] Relay Therapeut, Med Chem, 399 Binney St, Cambridge, MA 02139 USA
关键词
amino alcohols; C-O coupling; aryl alkyl ethers; bippyphos; palladium catalysis; REDUCTIVE ELIMINATION; 1,2-AMINO ALCOHOLS; ACTIVATED ARYL; NUCLEOPHILIC-SUBSTITUTION; PRACTICAL SYNTHESIS; CHIRAL AUXILIARIES; LIGANDS; BOND; DERIVATIVES; HALIDES;
D O I
10.1002/adsc.201901302
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Amine containing aryl ethers are common pharmacophore motifs that continue to emerge from drug discovery efforts. As amino alcohols are readily available building blocks, practical methodologies for incorporating them into more complex structures are highly desirable. We report our efforts to explore the application of Pd-catalyzed C-O coupling methods to the arylation of 1,2- and 1,3-amino alcohols. We established general and reliable conditions, under which we explored the scope and limitations of the transformation. The insights gained have been valuable in employing this methodology within a fast-moving drug discovery environment, which we anticipate will be of general interest to the synthesis and catalysis communities.
引用
收藏
页码:430 / 436
页数:7
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