Helicenes Built from Silacyclopentadienes via Ring-by-Ring Knitting of the Helical Framework

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F19%3A00500188" target="_blank" >RIV/61388963:_____/19:00500188 - isvavai.cz</a>
Alternative codes found
RIV/61388980:_____/19:00500188 RIV/00216275:25310/19:39915532
Result on the web
<a href="https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201811140" target="_blank" >https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201811140</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/anie.201811140" target="_blank" >10.1002/anie.201811140</a>

Result language
angličtina
Original language name
Helicenes Built from Silacyclopentadienes via Ring-by-Ring Knitting of the Helical Framework
Original language description
Despite the apparent diversity of the protocols developed for the synthesis of helicenes, they essentially follow the same strategy: the closure of one, or several, internal rings in a key step. Herein, we report the synthesis of a new family of the heterohelicenes consisting of fused silacyclopentadiene rings formed via a facile and novel process. The treatment of oligo(alkynilydenesilylene) precursors of type H2C=CH−(SiMe2−C≡C)n−R (n=3–7), bearing a vinyl group on the terminal silicon atom, with 9-borabicyclononane leads first to 1,2-hydroboration of the terminal double bond which then continues with a cascade of intramolecular 1,1-carboboration reactions accompanied with the closure of a new silole ring after each step affording the target silahelicenes with, currently, up to seven condensed silole rings and with excellent yields. According XRD analysis, the seven fused silole rings of the heptacyclic compound 11 b form an almost complete turn of a helix. The presented one-pot sequence of reactions is the first example of ring-by-ring knitting of a helical framework starting from easily available linear precursors.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry

Project
<a href="/en/project/GA17-22253S" target="_blank" >GA17-22253S: New family of helicenes based on fused silacyclopentadienes</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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