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Facile 1,1-Carboboration Reaction of a Diarylphosphino-substituted Conjugated Diyne with Tris(pentafluorophenyl)borane
| Content Provider | Semantic Scholar |
|---|---|
| Author | Feldhaus, Philipp Kehr, Gerald Fröhlich, Roland Daniliuc, Constantin G. Erker, Gerhard |
| Copyright Year | 2013 |
| Abstract | Bis(dimesitylphosphanyl)butadiyne (14) reacts with B(C6F5)3 by a 1,1-carboboration sequence. The selective attack at a single phosphanyl-alkyne moiety is observed. First a phosphirenium-borate zwitterion 15 is formed at r. t. Thermolysis (80 °C) results in the E-selective formation of the 1,1- carboboration product, the frustrated Lewis pair (FLP) E-16, which upon heating to 160 °C eventually undergoes isomerization followed by an internal nucleophilic aromatic substitution reaction to give the product 17 featuring a -B(F)(C6F5)2 substituent at the five-membered P-heterocycle. Finally, the FLP E-16 was reacted with n-butylisocyanide to yield the five-membered heterocyclic product 18, formed by P,B addition to the isonitrile carbon atom. Compounds 14, 15, 17, and 18 were characterized by X-ray crystal structure analyses Graphical Abstract Facile 1,1-Carboboration Reaction of a Diarylphosphino-substituted Conjugated Diyne with Tris(pentafluorophenyl)borane |
| Starting Page | 666 |
| Ending Page | 674 |
| Page Count | 9 |
| File Format | PDF HTM / HTML |
| DOI | 10.5560/znb.2013-3088 |
| Volume Number | 68 |
| Alternate Webpage(s) | http://www.degruyter.com/downloadpdf/j/znb.2013.68.issue-5-6/znb.2013-3088/znb.2013-3088.xml |
| Alternate Webpage(s) | http://www.znaturforsch.com/ab/v68b/ZNB130088-ESM.pdf |
| Alternate Webpage(s) | http://www.znaturforsch.com/s68b/s68b0666.pdf |
| Alternate Webpage(s) | https://doi.org/10.5560/znb.2013-3088 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
