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Synfacts 2020; 16(03): 0296
DOI: 10.1055/s-0039-1690391
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

Hydroamination of Olefins

Contributor(s):
Paul Knochel
,
Juri Skotnitzki
Yahata K. * Kaneko Y, Akai S. Osaka University, Japan
Cobalt-Catalyzed Intermolecular Markovnikov Hydroamination of Nonactivated Olefins: N 2-Selective Alkylation of Benzotriazole.

Org. Lett. 2020;
22: 598-603
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Further Information

Publication History

Publication Date:
18 February 2020 (online)

 
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Key words

cobalt catalysis - benzotriazoles - hydroamination - olefins

Significance

Yahata and co-workers report the Markovnikov hydroamination of several terminal and internal olefins using benzotriazoles in satisfactory to good yield and with high N 2 regioselectivity. The obtained isobenzotriazoles could be transformed into primary amines by reduction with zinc in high yields.


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Comment

A plausible reaction mechanism in which a Co(III) intermediate is generated by oxidation of Co(II) with TMFP-BF4 is proposed. After transmetalation with PhSiH3 and HAT with the olefin substrate, an intermediate alkyl-Co(III) is obtained. The latter is oxidized to a cationic Co(IV) species, which undergoes an SN2-like displacement with the generated silylated benzotriazole to afford the desired product.


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