Photocatalytic Umpolung Strategy for the Synthesis of α‑Amino Phosphine Oxides and Deuterated Derivatives

Direct, economical, and green synthesis of deuterated α-amino phosphine oxides remains an elusive challenge in synthetic chemistry. Herein, we report a visible-light-driven umpolung strategy for synthesizing deuterated α-amino phosphine oxides from isocyanide using 1,2,3,5-tetrakis­(carbazol-9-yl)-4...

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Bibliographic Details
Published inOrganic letters Vol. 25; no. 44; pp. 8016 - 8021
Main Authors Ma, Chunhua, Li, Xiaofeng, Chen, Xiya, He, Xing, Zhang, Shu-Ting, Jiang, Yu-Qin, Yu, Bing
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 10.11.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
2-ISOCYANOBIPHENYLS
KABACHNIK-FIELDS REACTION
PHOSPHONATES
RADICAL C-P
ISOCYANIDES
GENERATION
EFFICIENT
CYCLIZATION
AMINOPHOSPHONATES
SOLVENT
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Summary:Direct, economical, and green synthesis of deuterated α-amino phosphine oxides remains an elusive challenge in synthetic chemistry. Herein, we report a visible-light-driven umpolung strategy for synthesizing deuterated α-amino phosphine oxides from isocyanide using 1,2,3,5-tetrakis­(carbazol-9-yl)-4,6-dicyanobenzene as the photocatalyst and D2O as the deuterium source. Moreover, the streamlined and sustainable methodology can be applied in the modification of amino acids, natural products, and drugs. The strong antiproliferative activity of the desired products indicates that the method could provide a novel privileged scaffold for antitumor drug development.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03193