Rational Catalysis Design on the Basis of Mechanistic Understanding: Highly Efficient Pd-Catalyzed Cyanation of Aryl Bromides with NaCN in Recyclable Solvents
- 23 June 2011
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 133 (28), 10999-11005
- https://doi.org/10.1021/ja2042035
Abstract
Rational catalysis design on the basis of a detailed mechanistic understanding has been used to successfully develop the first efficient general Pd-catalyzed aromatic cyanation reaction under the highly sought after practicable conditions: (i) MCN (M = Na or K) as a cyanide source; (ii) low-boiling recyclable solvents; and (iii) minimal quantities of inexpensive, nontoxic promoters. The developed catalytic reaction converts aromatic bromides to the corresponding nitriles in 88-99% isolated yield with NaCN and 0.5-1.0 mol % of a t-Bu(3)P-monoligated Pd catalyst in MeCN-THF within 2 h at 70 °C. The process exhibits high functional group tolerance.This publication has 63 references indexed in Scilit:
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