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Stereospecific palladium-promoted vicinal diamination of olefins

✍ Scribed by Jan-E. Bäckvall

Book ID
104236933
Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
238 KB
Volume
19
Category
Article
ISSN
0040-4039

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✦ Synopsis

We have recently reported on the palladium-promoted oxyamination' and aziridination 2 of olefins. These transformations were obtained by aminopalladation3 of the olefin followed by an oxidative cleavage of the palladium-carbon bond in the adduct.

In the oxyamination study it was found' that vicinal diamines are formed as side-products from terminal olefins in the presence of excess amine. This observation led us to study the oxidation of 8-aminoalkylpalladium compounds 1 in the presence of amine, using different oxidizing agents.

We report here that olefins can be stereospecifically transformed into vicinal diamines 2 by an aminopalladation-oxidation sequence (es l), using oxidants such as bromine, m-chloroperbenzoic acid (MCPBA), and N-bromosuccinimide (NBS).

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