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Silylation of C–H bonds in aromatic heterocycles by an Earth-abundant metal catalyst

Overview of attention for article published in Nature, February 2015
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About this Attention Score

  • In the top 5% of all research outputs scored by Altmetric
  • High Attention Score compared to outputs of the same age (99th percentile)
  • Good Attention Score compared to outputs of the same age and source (77th percentile)

Mentioned by

news
21 news outlets
blogs
3 blogs
twitter
34 tweeters
patent
12 patents
facebook
4 Facebook pages
wikipedia
2 Wikipedia pages

Citations

dimensions_citation
301 Dimensions

Readers on

mendeley
345 Mendeley
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Title
Silylation of C–H bonds in aromatic heterocycles by an Earth-abundant metal catalyst
Published in
Nature, February 2015
DOI 10.1038/nature14126
Pubmed ID
Authors

Anton A. Toutov, Wen-Bo Liu, Kerry N. Betz, Alexey Fedorov, Brian M. Stoltz, Robert H. Grubbs

Abstract

Heteroaromatic compounds containing carbon-silicon (C-Si) bonds are of great interest in the fields of organic electronics and photonics, drug discovery, nuclear medicine and complex molecule synthesis, because these compounds have very useful physicochemical properties. Many of the methods now used to construct heteroaromatic C-Si bonds involve stoichiometric reactions between heteroaryl organometallic species and silicon electrophiles or direct, transition-metal-catalysed intermolecular carbon-hydrogen (C-H) silylation using rhodium or iridium complexes in the presence of excess hydrogen acceptors. Both approaches are useful, but their limitations include functional group incompatibility, narrow scope of application, high cost and low availability of the catalysts, and unproven scalability. For this reason, a new and general catalytic approach to heteroaromatic C-Si bond construction that avoids such limitations is highly desirable. Here we report an example of cross-dehydrogenative heteroaromatic C-H functionalization catalysed by an Earth-abundant alkali metal species. We found that readily available and inexpensive potassium tert-butoxide catalyses the direct silylation of aromatic heterocycles with hydrosilanes, furnishing heteroarylsilanes in a single step. The silylation proceeds under mild conditions, in the absence of hydrogen acceptors, ligands or additives, and is scalable to greater than 100 grams under optionally solvent-free conditions. Substrate classes that are difficult to activate with precious metal catalysts are silylated in good yield and with excellent regioselectivity. The derived heteroarylsilane products readily engage in versatile transformations enabling new synthetic strategies for heteroaromatic elaboration, and are useful in their own right in pharmaceutical and materials science applications.

Twitter Demographics

The data shown below were collected from the profiles of 34 tweeters who shared this research output. Click here to find out more about how the information was compiled.

Mendeley readers

The data shown below were compiled from readership statistics for 345 Mendeley readers of this research output. Click here to see the associated Mendeley record.

Geographical breakdown

Country Count As %
United States 3 <1%
France 2 <1%
Switzerland 2 <1%
United Kingdom 2 <1%
Japan 2 <1%
Belgium 1 <1%
South Africa 1 <1%
India 1 <1%
Poland 1 <1%
Other 0 0%
Unknown 330 96%

Demographic breakdown

Readers by professional status Count As %
Student > Ph. D. Student 98 28%
Researcher 67 19%
Student > Master 49 14%
Student > Bachelor 35 10%
Professor > Associate Professor 17 5%
Other 52 15%
Unknown 27 8%
Readers by discipline Count As %
Chemistry 277 80%
Materials Science 6 2%
Engineering 6 2%
Agricultural and Biological Sciences 5 1%
Biochemistry, Genetics and Molecular Biology 4 1%
Other 15 4%
Unknown 32 9%

Attention Score in Context

This research output has an Altmetric Attention Score of 211. This is our high-level measure of the quality and quantity of online attention that it has received. This Attention Score, as well as the ranking and number of research outputs shown below, was calculated when the research output was last mentioned on 26 April 2022.
All research outputs
#140,692
of 21,944,731 outputs
Outputs from Nature
#9,877
of 89,096 outputs
Outputs of similar age
#1,802
of 324,592 outputs
Outputs of similar age from Nature
#208
of 907 outputs
Altmetric has tracked 21,944,731 research outputs across all sources so far. Compared to these this one has done particularly well and is in the 99th percentile: it's in the top 5% of all research outputs ever tracked by Altmetric.
So far Altmetric has tracked 89,096 research outputs from this source. They typically receive a lot more attention than average, with a mean Attention Score of 98.6. This one has done well, scoring higher than 88% of its peers.
Older research outputs will score higher simply because they've had more time to accumulate mentions. To account for age we can compare this Altmetric Attention Score to the 324,592 tracked outputs that were published within six weeks on either side of this one in any source. This one has done particularly well, scoring higher than 99% of its contemporaries.
We're also able to compare this research output to 907 others from the same source and published within six weeks on either side of this one. This one has done well, scoring higher than 77% of its contemporaries.