Carbon-carbon bond forming reactions of acetylenic esters and ketones within frustrated phosphane/borane Lewis pair frameworks

The three-component reactions of bulky diarylbutenylphosphanes with dimethyl acetylenedicarboxylate (1a) and the strong boron Lewis acid B(C6F5)3 give the ylide-substituted cyclopropane derivatives 26. The acetylenic ester 1a and ketone 1b react with oligomethylene bridged frustrated phosphane/boran...

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Bibliographic Details
Published in:Dalton transactions : an international journal of inorganic chemistry 2019-08, Vol.48 (31), p.11921-11926
Main Authors: Wang, Long, Li, Jun, Deng, Dongsheng, Daniliuc, Constantin G, Mück-Lichtenfeld, Christian, Kehr, Gerald, Erker, Gerhard
Format: Article
Language:English
Subjects:
Boron
Carbon
Crystallography
Cyclopropane
Esters
Ketones
Lewis acid
Reaction products
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Summary:The three-component reactions of bulky diarylbutenylphosphanes with dimethyl acetylenedicarboxylate (1a) and the strong boron Lewis acid B(C6F5)3 give the ylide-substituted cyclopropane derivatives 26. The acetylenic ester 1a and ketone 1b react with oligomethylene bridged frustrated phosphane/borane Lewis pairs to give the bicyclic C-H insertion/C-C coupling reaction products. The formal carbene products are formed by means of stepwise sequences involving polar intermediate.
ISSN:1477-9226
1477-9234
DOI:10.1039/c9dt02624j