Developing carbon Lewis base/boron Lewis acid frustrated Lewis pair chemistry derived from conjugated dienamines

摘要

Several dienamines R2N-CH=CH-CH=CMe2 react with Piers' borane by HB(C6F5)(2) addition to the terminal -CH=CMe2 unit to form the isopropyl substituted products 14. The strongly electrophilic -B(C6F5)(2) functionality at the C3 position of the chain shows a marked contact to the adjacent enamine beta-carbon atom C2. This generates a pronounced C/B FLP character which chemically comes to bear in the 1,2 addition reactions to the C=O bond of benzaldehyde or the -C N bonds of a series of alkylcyanides. In some cases, the formation of uncommon rearrangement products is observed. (C) 2018 Elsevier Ltd. All rights reserved.