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The Phosphinoboration Reaction
Author(s) -
Daley Erika N.,
Vogels Christopher M.,
Geier Stephen J.,
Decken Andreas,
Doherty Simon,
Westcott Stephen A.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201410033
Subject(s) - regioselectivity , aldimine , chemistry , reactivity (psychology) , catalysis , single bond , transition metal , double bond , stereochemistry , medicinal chemistry , organic chemistry , group (periodic table) , medicine , alternative medicine , pathology
The synthesis of phosphinoboronate esters containing a single PB bond is reported, together with preliminary reactivity studies towards a range of organic substrates. These compounds add readily to aldehydes, ketones, aldimines, and α,β‐unsaturated enones to give primarily the corresponding 1,2‐addition products containing a new PC bond. The first examples of transition‐metal‐catalyzed phosphinoborations of C‐C multiple bonds in which PC and BC bonds are formed in a single step are also disclosed; allenes react by a highly regioselective 1,2‐addition whereas terminal alkynes undergo a formal 1,1‐addition.