Mechanism of phosphinidene complex arylation by arylboronic acids
The arylation reaction of terminal phosphinidene complexes [RP-W(CO)5] by arylboronic acids is very sensitive to steric hindrance and the electronic properties of the substituents on the aryl ring. On the basis of DFT calculations and additional experiments, it seems that the mechanism involves firs...
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sg-ntu-dr.10356-1031032023-02-28T19:42:42Z Mechanism of phosphinidene complex arylation by arylboronic acids Ng, Yong Xiang Mathey, Francois School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry The arylation reaction of terminal phosphinidene complexes [RP-W(CO)5] by arylboronic acids is very sensitive to steric hindrance and the electronic properties of the substituents on the aryl ring. On the basis of DFT calculations and additional experiments, it seems that the mechanism involves first an insertion of the phosphinidene into one of the B–O bonds, followed by an intramolecular nucleophilic attack of the aryl group onto the P–OH bond promoted by the potassium phosphate. The [1,2]-aryl shift from B to P cannot be reproduced with an alkyl group. Accepted version 2014-12-09T05:58:45Z 2019-12-06T21:05:40Z 2014-12-09T05:58:45Z 2019-12-06T21:05:40Z 2014 2014 Journal Article Ng, Y. X., & Mathey, F. (2014). Mechanism of phosphinidene complex arylation by arylboronic acids. Organometallics, 33(5), 1322-1324. https://hdl.handle.net/10356/103103 http://hdl.handle.net/10220/24380 10.1021/om5001138 en Organometallics © 2014 American Chemical Society. This is the author created version of a work that has been peer reviewed and accepted for publication by Organometallics, American Chemical Society. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [Article DOI: http://dx.doi.org/10.1021/om5001138]. 12 p. application/pdf |
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DRNTU::Science::Chemistry::Organic chemistry Ng, Yong Xiang Mathey, Francois Mechanism of phosphinidene complex arylation by arylboronic acids |
| description |
The arylation reaction of terminal phosphinidene complexes [RP-W(CO)5] by arylboronic acids is very sensitive to steric hindrance and the electronic properties of the substituents on the aryl ring. On the basis of DFT calculations and additional experiments, it seems that the mechanism involves first an insertion of the phosphinidene into one of the B–O bonds, followed by an intramolecular nucleophilic attack of the aryl group onto the P–OH bond promoted by the potassium phosphate. The [1,2]-aryl shift from B to P cannot be reproduced with an alkyl group. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Ng, Yong Xiang Mathey, Francois |
| format |
Article |
| author |
Ng, Yong Xiang Mathey, Francois |
| author_sort |
Ng, Yong Xiang |
| title |
Mechanism of phosphinidene complex arylation by arylboronic acids |
| title_short |
Mechanism of phosphinidene complex arylation by arylboronic acids |
| title_full |
Mechanism of phosphinidene complex arylation by arylboronic acids |
| title_fullStr |
Mechanism of phosphinidene complex arylation by arylboronic acids |
| title_full_unstemmed |
Mechanism of phosphinidene complex arylation by arylboronic acids |
| title_sort |
mechanism of phosphinidene complex arylation by arylboronic acids |
| publishDate |
2014 |
| url |
https://hdl.handle.net/10356/103103 http://hdl.handle.net/10220/24380 |
| _version_ |
1759855552006979584 |