Synfacts 2020; 16(09): 1085
DOI: 10.1055/s-0040-1706757
Polymer-Supported Synthesis

α-Arylation of Nitriles Catalyzed by Palladium Nanoparticles in Proline-Based Micelles

Contributor(s):
Yasuhiro Uozumi
,
Ryoko Niimi
Bihani M, Ansari TN, Finck L, Bora PP, Jasinski JB, Pavuluri B, Leahy DK, *, Handa S. * Takeda Pharmaceuticals International, Cambridge and University of Louisville, USA
Scalable α-Arylation of Nitriles in Aqueous Micelles Using Ultrasmall Pd Nanoparticles: Surprising Formation of Carbanions in Water.

ACS Catal. 2020;
10: 6816-6821
 

Significance

Palladium nanoparticles in micelles of a proline-based amphiphile ([email protected]), generated in situ (eq. 1), promoted the α-arylation of arylacetonitriles with aryl bromides to give the corresponding α-arylated products in up to 92% yield (eq. 2).


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Comment

The PdNPs were characterized by means of 31P NMR, HRTEM, and EDAX analyses. A heterogeneous and amphiphilic vesicular Pd catalyst has been previously reported (see, for example: G. Hamasaka, T. Muto, Y. Uozumi Angew. Chem. Int. Ed. 2011, 50, 4876).


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Publication History

Publication Date:
18 August 2020 (online)

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