Facile synthesis of α-aminophosphine oxides from diarylphosphine oxides, arynes and formamides

The straightforward synthesis of α-amino phosphine oxides via three-component reactions involving arynes, formamides and diarylphosphine oxides is disclosed. This method employs the aryne to activate formamide, without an external activating reagent, which is operationally simple under mild conditio...

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Published inChemical communications (Cambridge, England) Vol. 57; no. 75; pp. 9578 - 9581
Main Authors Huang, Wen-Bin, Qiu, Li-Qi, Ren, Fang-Yu, He, Liang-Nian
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 25.09.2021
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Multidisciplinary
Crystallography
Cycloaddition
Oxides
Phosphine oxide
Physical Sciences
Reagents
Science & Technology
AMINATION
ETHERS
ACIDS
CATALYST-FREE
AMINO PHOSPHONATES
BOND FUNCTIONALIZATION
SECONDARY
INHIBITORS
ACCESS
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Summary:The straightforward synthesis of α-amino phosphine oxides via three-component reactions involving arynes, formamides and diarylphosphine oxides is disclosed. This method employs the aryne to activate formamide, without an external activating reagent, which is operationally simple under mild conditions with high efficiency. Furthermore, mechanistic perception suggests a cascade sequence including formal [2 + 2] cycloaddition of the aryne with a C&z.dbd;O bond, and a 1,4-addition of the H-P(O) compounds to the enamine intermediates. The straightforward synthesis of α-amino phosphine oxides via three-component reactions involving arynes, formamides and diarylphosphine oxides is disclosed.
Bibliography:Electronic supplementary information (ESI) available. CCDC
For ESI and crystallographic data in CIF or other electronic format see DOI
2059146
10.1039/d1cc04101k
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc04101k