Dimethylamine adducts of allylic triorganoboranes as effective reagents for Petasis-type homoallylation of primary amines with formaldehyde

Dimethylamine adducts of triallyl-, triprenyl- and trans-cinnamyl(dipropyl)borane are effective reagents for mild homoallylation of primary amines with aqueous formaldehyde in MeOH without an inert atmosphere. A new concept is proposed for the explanation of the high stability of allylborane-amine a...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2018-10, Vol.16 (39), p.7115-7119
Main Authors: Kuznetsov, Nikolai Yu, Tikhov, Rabdan M, Strelkova, Tatiana V, Bubnov, Yuri N
Format: Article
Language:English
Subjects:
Adducts
Amines
Formaldehyde
Inert atmospheres
NMR
Nuclear magnetic resonance
Reagents
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Summary:Dimethylamine adducts of triallyl-, triprenyl- and trans-cinnamyl(dipropyl)borane are effective reagents for mild homoallylation of primary amines with aqueous formaldehyde in MeOH without an inert atmosphere. A new concept is proposed for the explanation of the high stability of allylborane-amine adducts in aqueous MeOH.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob02152j