Mechanistic insights into the triazolylidene-catalysed Stetter and benzoin reactions: role of the N-aryl substituent
The in situobservation, isolation and reversible formation of intermediate 3-(hydroxybenzyl)azolium salts derived from NHC addition to a range of substituted benzaldehydes is probed. Equilibrium constants for the formation of these 3-(hydroxybenzyl)azolium salts, as well as rate constants of hydroge...
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| Veröffentlicht in: | Chemical science (Cambridge) 2013-01, Vol.4 (4), p.1514-1522 |
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| container_title | Chemical science (Cambridge) |
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| creator | Collett, Christopher J. Massey, Richard S. Maguire, Oliver R. Batsanov, Andrei S. O'Donoghue, AnnMarie C. Smith, Andrew D. |
| description | The in situobservation, isolation and reversible formation of intermediate 3-(hydroxybenzyl)azolium salts derived from NHC addition to a range of substituted benzaldehydes is probed. Equilibrium constants for the formation of these 3-(hydroxybenzyl)azolium salts, as well as rate constants of hydrogen-deuterium exchange (k sub(ex)) at C( alpha ) of these intermediates for a range of N-aryl triazolinylidenes is reported. These combined studies give insight into the preference of N-pentafluorophenyl NHCs to participate in benzoin and Stetter reaction processes. |
| doi_str_mv | 10.1039/c2sc22137c |
| format | Article |
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| ispartof | Chemical science (Cambridge), 2013-01, Vol.4 (4), p.1514-1522 |
| issn | 2041-6520 2041-6539 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1323241762 |
| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Benzoin Chemical equilibrium Rate constants |
| title | Mechanistic insights into the triazolylidene-catalysed Stetter and benzoin reactions: role of the N-aryl substituent |
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