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Selective C-C coupling at a Pt(IV) centre : 100% preference for sp2-sp3 over sp3-sp3
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Shaw, Paul Anthony and Rourke, Jonathan (2017) Selective C-C coupling at a Pt(IV) centre : 100% preference for sp2-sp3 over sp3-sp3. Dalton Transactions, 46 (14). 4768--4776 . doi:10.1039/C7DT00328E ISSN 1477-9226.
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Official URL: http://dx.doi.org/10.1039/C7DT00328E
Abstract
The oxidative addition of three different organic halides to the non-symmetric platinum(II) mer coordinated dicyclometallated C^N^C complex 1 yielded short-lived six-coordinate platinum(IV) complexes 2(R), with the incoming groups trans across the platinum centre. A spontaneous reductive coupling reaction then occurred with, in each case, a completely chemoselective sp2-sp3 coupling, and exclusively gave R-3, with the newly introduced R group bonded to the previously cyclometallated aryl ring. Following a recyclometallation reaction, the oxidative addition/reductive elimination cycle was repeated and gave the same selectivity. A one-pot route to doubly alkylating the aryl ring was developed. The observed selectivity might have been predicted on the normal basis of a steric barrier associated with non-flat sp3 hybridised groups, but we suggest that it arises from the stereochemistry at the metal, and the orientation of the ligands.
Item Type: | Journal Article | ||||||||||
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Subjects: | Q Science > QD Chemistry | ||||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||||||
Library of Congress Subject Headings (LCSH): | Hydrocarbons, Catalysis, Platinum--Carbon content, Organometallic compounds | ||||||||||
Journal or Publication Title: | Dalton Transactions | ||||||||||
Publisher: | Royal Society of Chemistry | ||||||||||
ISSN: | 1477-9226 | ||||||||||
Official Date: | 14 April 2017 | ||||||||||
Dates: |
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Volume: | 46 | ||||||||||
Number: | 14 | ||||||||||
Page Range: | 4768--4776 | ||||||||||
DOI: | 10.1039/C7DT00328E | ||||||||||
Status: | Peer Reviewed | ||||||||||
Publication Status: | Published | ||||||||||
Access rights to Published version: | Restricted or Subscription Access | ||||||||||
Date of first compliant deposit: | 21 March 2017 | ||||||||||
Date of first compliant Open Access: | 21 March 2018 | ||||||||||
Funder: | Engineering and Physical Sciences Research Council (EPSRC) |
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