Loading...
Please wait, while we are loading the content...
Palladium-Catalyzed, Ortho-Selective C-H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Das, Riki Kapur, Manmohan |
| Copyright Year | 2018 |
| Abstract | Aryl halides are an indispensably important class of compounds, due to their role as precursors in the synthesis of organometallic reagents 1 and nucleophilic substitution reaction. 2 In addition, with the advent of cross-coupling chemistry 3 the importance of aryl halides increased tremendously, and hence they can be classified as the core building blocks of organic synthesis. Traditional methods to access aryl halides involve Sandmeyer reaction 4 or electrophilic aromatic substitution 5 and these usually suffer from several disadvantages, such as harsh reaction conditions, dangerous operations, toxic reagents and low selectivity. Over the last decade, metal catalyzed C-H halogenation of arenes has emerged as a modern and environmentally friendly tool for organic synthesis. In this context we will discuss herein a palladium catalyzed, ortho-selective C-H halogenation. The highlight of the work is the highly selective C(sp2)–H functionalization of benzyl nitriles in presence of an activated C(sp3)-H bond, which results in good yields of the halogenated products with excellent regioselectivity. Along with benzyl nitriles, aryl Weinreb amides and anilides have been evaluated for the transformation using aprotic conditions. Mechanistic studies yield interesting aspects with respect to the pathway of the reaction and the directing group abilities. |
| Starting Page | 14218 |
| Ending Page | 14218 |
| Page Count | 1 |
| File Format | PDF HTM / HTML |
| DOI | 10.1021/acs.joc.8b02652 |
| PubMed reference number | 30376331 |
| Journal | Medline |
| Volume Number | 83 |
| Issue Number | 22 |
| Alternate Webpage(s) | http://conf.iiserb.ac.in/IICM2017/poster-abstract/PP%2014_Ms.%20Riki%20Das_IISER%20Bhopal.pdf |
| Alternate Webpage(s) | https://doi.org/10.1021/acs.joc.8b02652 |
| Journal | The Journal of organic chemistry |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
