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| Title |
Amine‐Catalyzed Highly Regioselective and Stereoselective C(sp2)–C(sp2) Cross‐Coupling of Naphthols with trans‐α,β‐Unsaturated Aldehydes
|
|---|---|
| Published in |
Chemistry - An Asian Journal, July 2015
|
| DOI | 10.1002/asia.201500460 |
| Pubmed ID | |
| Authors |
Yang Hu, Yueyue Ma, Rengwei Sun, Xinhong Yu, Hexin Xie, Wei Wang |
| Abstract |
We describe a metal-free C(sp2)-C(sp2) cross-coupling approach to highly congested (E) α-naphtholylenals from simple naphthols and enals.The mild reaction conditions by the use of PHBP as the bromination reagent in the presence of piperidine or diphenylprolinol TMS ether as promoters enable the process in good yields and with high chemo-, regio- and stereo-selectivities.The process involves an unprecedented pathway of in situ regio-selective 4-bromination of 1-naphthols and the subsequent unusual aromatic nucleophilic substitution of the resulted 4-bromo-1-naphthols with the α-C(sp2) of enals via a Michael-type Friedel-Crafts alkylation-dearomatization followed by a cyclopropanation-ring opening cascade process.The noteworthy features of this strategy are highlighted by its highly efficient creation of a C(sp2)-C(sp2) bond from readily available unfunctionalized naphthols and enals catalyzed by non-metal, readily available cyclic secondary amines under mild reaction conditions. |
X Demographics
The data shown below were collected from the profile of 1 X user who shared this research output. Click here to find out more about how the information was compiled.
Geographical breakdown
| Country | Count | As % |
|---|---|---|
| Unknown | 1 | 100% |
Demographic breakdown
| Type | Count | As % |
|---|---|---|
| Science communicators (journalists, bloggers, editors) | 1 | 100% |
Mendeley readers
The data shown below were compiled from readership statistics for 9 Mendeley readers of this research output. Click here to see the associated Mendeley record.
Geographical breakdown
| Country | Count | As % |
|---|---|---|
| Japan | 1 | 11% |
| Unknown | 8 | 89% |
Demographic breakdown
| Readers by professional status | Count | As % |
|---|---|---|
| Student > Ph. D. Student | 2 | 22% |
| Professor > Associate Professor | 2 | 22% |
| Researcher | 1 | 11% |
| Student > Doctoral Student | 1 | 11% |
| Unknown | 3 | 33% |
| Readers by discipline | Count | As % |
|---|---|---|
| Chemistry | 6 | 67% |
| Unknown | 3 | 33% |
Attention Score in Context
This research output has an Altmetric Attention Score of 1. 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 14 July 2015.
All research outputs
#22,029,081
of 24,577,646 outputs
Outputs from Chemistry - An Asian Journal
#4,866
of 5,884 outputs
Outputs of similar age
#227,914
of 267,697 outputs
Outputs of similar age from Chemistry - An Asian Journal
#98
of 119 outputs
Altmetric has tracked 24,577,646 research outputs across all sources so far. This one is in the 1st percentile – i.e., 1% of other outputs scored the same or lower than it.
So far Altmetric has tracked 5,884 research outputs from this source. They receive a mean Attention Score of 1.8. This one is in the 1st percentile – i.e., 1% of its peers scored the same or lower than it.
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We're also able to compare this research output to 119 others from the same source and published within six weeks on either side of this one. This one is in the 1st percentile – i.e., 1% of its contemporaries scored the same or lower than it.