Rational Catalysis Design on the Basis of Mechanistic Understanding: Highly Efficient Pd-Catalyzed Cyanation of Aryl Bromides with NaCN in Recyclable Solvents
Alexander V. Ushkov and Vladimir V. Grushin*
*The Institute of Chemical Research of Catalonia (ICIQ), Tarragona, Spain, Email: vgrushiniciq.es
A. V. Ushkov, V. V. Grushin, J. Am. Chem. Soc., 2011, 133, 10999-11005.
DOI: 10.1021/ja2042035 (free Supporting Information)
A t-Bu3P-monoligated Pd catalyst in MeCN-THF enabled an efficient general aromatic cyanation reaction under practicable conditions using NaCN as cyanide source, low-boiling recyclable solvents, and minimal quantities of inexpensive, nontoxic promoters. The reaction converts aromatic bromides to the corresponding nitriles in very good yield in short reaction time and tolerates many functional groups.
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