Direct Oxidation of Aliphatic C-H Bonds in Amino P-Containing Molecules under Transition-Metal-Free Conditions

By employing a simple, inexpensive, and transition metal-free oxidation system, secondary C-H bonds in a series of phthaloyl protected primary amines and amino acid derivatives were oxidized to carbonyls with good regioselectivities. This method could also be applied to oxidize tertiary C-H bonds an...

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Bibliographic Details
Published inOrganic letters Vol. 18; no. 6; pp. 1234 - 1237
Main Authors Li, Xin, Che, Xing, Chen, Gui-Hua, Zhang, Jun, Yan, Jia-Lei, Zhang, Yun-Fei, Zhang, Li-Sheng, Hsu, Chao-Ping, Gao, Yi Qin, Shi, Zhang-Jie
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 18.03.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
C(SP)-H BONDS
PEPTIDES
ACETOXYLATION
HYDROXYLATION
INTRAMOLECULAR OXIDATION
STEREOSELECTIVE-SYNTHESIS
CATALYST
SELECTIVITY
HIGHLY EFFICIENT
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Summary:By employing a simple, inexpensive, and transition metal-free oxidation system, secondary C-H bonds in a series of phthaloyl protected primary amines and amino acid derivatives were oxidized to carbonyls with good regioselectivities. This method could also be applied to oxidize tertiary C-H bonds and modify synthetic dip eptides.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b03690