Palladium-Catalyzed Decarbonylation of Amino Acid Derivatives via C-C Bond and C-N Bond Dual Activations

被引:2
|
作者
Wu, Jiamin [1 ]
Zhang, Jinli [1 ]
Jiao, Yongjuan [1 ]
Deng, Gongtao [1 ]
Li, Yingmei [2 ]
Zhang, Zhengyu [1 ]
Jiang, Yaojia [1 ,2 ]
机构
[1] Nanjing Tech Univ, Coll Food Sci & Light Ind, Sch Chem & Mol Engn, Inst Adv Synth, Nanjing 211816, Peoples R China
[2] Guizhou Univ, Lab Breeding Base Green Pesticide & Agr Bioengn, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 23期
基金
中国国家自然科学基金;
关键词
COUPLING REACTIONS; H BONDS; ARYLATION; PD(II); AMIDES; CHELATION;
D O I
10.1021/acs.joc.1c02162
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A unique decarbonylation of an amino acid derivative catalytic system has been established via palladium-catalyzed C-C bond and C-N bond dual activations. By employing 8-aminoquinoline as the directing group, this transformation has been found to facilitate the high chemoselectivity to decarbonylation of amino acid derivatives rather than intramolecular deamination or cross-dehydrogenative coupling reactions. This method provides a straightforward avenue for constructing diverse functionalized amide compounds in good to excellent yields. We proposed a possible reaction pathway that may go through the C-C bond and C-N bond dual activations on the basis of the mechanistic studies.
引用
收藏
页码:17462 / 17470
页数:9
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