| Title |
Iron(II)-Catalyzed Azidotrifluoromethylation of Olefins and N‑Heterocycles for Expedient Vicinal Trifluoromethyl Amine Synthesis
|
|---|---|
| Published in |
ACS Catalysis, April 2018
|
| DOI | 10.1021/acscatal.8b01253 |
| Pubmed ID | |
| Authors |
Cheng-Liang Zhu, Cheng Wang, Qi-Xue Qin, Sam Yruegas, Caleb D. Martin, Hao Xu |
| Abstract |
We report herein an iron-catalyzed azidotrifluoromethylation method for expedient vicinal trifluoromethyl primary-amine synthesis. This method is effective for a broad range of olefins and N-heterocycles, and it facilitates efficient synthesis of a wide variety of vicinal trifluoromethyl primary amines, including those that prove difficult to synthesize with existing approaches. Our preliminary mechanistic studies revealed that the catalyst-promoted azido-group transfer proceeds through a carbo-radical instead of a carbocation species. Characterization of an active iron catalyst through X-ray crystallographic studies suggests that in situ generated, structurally novel iron-azide complexes promote the oxidant activation and selective azido-group transfer. |
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X Demographics
Geographical breakdown
| Country | Count | As % |
|---|---|---|
| United States | 2 | 100% |
Demographic breakdown
| Type | Count | As % |
|---|---|---|
| Scientists | 1 | 50% |
| Members of the public | 1 | 50% |
Mendeley demographics
Geographical breakdown
| Country | Count | As % |
|---|---|---|
| Unknown | 22 | 100% |
Demographic breakdown
| Readers by professional status | Count | As % |
|---|---|---|
| Student > Ph. D. Student | 4 | 18% |
| Student > Master | 3 | 14% |
| Researcher | 3 | 14% |
| Student > Doctoral Student | 2 | 9% |
| Student > Bachelor | 2 | 9% |
| Other | 3 | 14% |
| Unknown | 5 | 23% |
| Readers by discipline | Count | As % |
|---|---|---|
| Chemistry | 17 | 77% |
| Unknown | 5 | 23% |