Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 37, Pages 13664-13667Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja4073172
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Funding
- NIH [R01-GM100143]
- NSF [CHE-1048642, CHE-0342998]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1048642] Funding Source: National Science Foundation
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Homogeneous Pd catalysts have been identified for the conversion of cyclohexenone and tetralone O-pivaloyl oximes to the corresponding primary anilines and 1-aminonaphthalenes. This method is inspired by the Semmler-Wolff reaction, a classic method that exhibits limited synthetic utility owing to its forcing conditions, narrow scope, and low product yields. The oxime N-O bond undergoes oxidative addition to Pd-0(PCy3)(2), and the product of this step has been characterized by X-ray crystallography and shown to undergo dehydrogenation to afford the aniline product.
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