Oxidation-Reduction Condensation of Diazaphosphites for Carbon-Heteroatom Bond Formation Based on Mitsunobu Mechanism

被引:10
|
作者
Huang, Hai [1 ,2 ]
Kang, Jun Yong [1 ]
机构
[1] Univ Nevada, Dept Chem & Biochem, 4505 South Maryland Pkwy, Las Vegas, NV 89154 USA
[2] Nanjing Tech Univ, Dept Appl Chem, Coll Chem & Mol Engn, 30 Puzhu Rd S, Nanjing 211816, Jiangsu, Peoples R China
关键词
ALKYL ARYL SULFIDES; N-ALKYLATION; DIETHYL AZODICARBOXYLATE; PHOSPHORIC-ACID; TERT-ALCOHOLS; AMINES; AMINATION; HYDROAMINATION; ALDEHYDES; DIPHENYLPHOSPHINITES;
D O I
10.1021/acs.orglett.6b03709
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient oxidation-reduction condensation reaction of diazaphosphites with various nonacidic pronudeophiles in the presence of DIAD as a weak oxidant has been developed for carbon-heteroatom bond formation. This mild process affords structurally diverse tertiary amines, secondary amines, esters, ethers, and thioethers in moderate to excellent yields. The selective synthesis of secondary amines from primary amines has been achieved. Importantly, a practical application to the synthesis of antiparkinsonian agent piribedil has been demonstrated.
引用
收藏
页码:544 / 547
页数:4
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