Superfast Formation of C(sp2)−N, C(sp2)−P, and C(sp2)−S Vinylic Bonds in Water Microdroplets
Yifan Meng
Department of Chemistry, Stanford University, Stanford, CA 94305 USA
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Richard N. Zare
Department of Chemistry, Stanford University, Stanford, CA 94305 USA
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Elumalai Gnanamani
Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, 247667 India
Search for more papers by this authorYifan Meng
Department of Chemistry, Stanford University, Stanford, CA 94305 USA
Search for more papers by this authorCorresponding Author
Richard N. Zare
Department of Chemistry, Stanford University, Stanford, CA 94305 USA
Search for more papers by this authorCorresponding Author
Elumalai Gnanamani
Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, 247667 India
Search for more papers by this authorAbstract
We report examples of C(sp2)−N, C(sp2)−S, and C(sp2)−P bond-forming transformations in water microdroplets at room temperature and atmospheric pressure using N2 as a nebulizing gas. When an aqueous solution of vinylic acid and amine is electrosprayed (+3 kV), the corresponding C(sp2)−N product is formed in a single step, which was characterized using mass spectrometry (MS) and tandem mass spectrometry (MS2). The scope of this reaction was extended to other amines and other unsaturated acids, including acrylic (CH2=CHCOOH) and crotonic (CH3CH=CHCOOH) acids. We also found that thiols and phosphines are viable nucleophiles, and the corresponding C(sp2)−S and C(sp2)−P products are observed in positive ion mode using MS and MS2.
Open Research
Data Availability Statement
The data that support the findings of this study are available from the corresponding author upon reasonable request.
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