2011
DOI: 10.1002/anie.201101051
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Reaction of Frustrated Lewis Pairs with Conjugated Ynones‐Selective Hydrogenation of the Carbon–Carbon Triple Bond

Abstract: Frustrated, but not frustrating: Frustrated Lewis pairs (FLPs) can undergo selective 1,4‐addition reactions with conjugated ynones (see scheme). Upon FLP dihydrogen activation selective hydrogenation of the carbon–carbon triple bond can be achieved, in one case even catalytically.

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Cited by 178 publications
(88 citation statements)
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“…15 Only recently were highly selective metal-free catalysts for alkyne hydrogenation reported. 6,[16][17][18][19][20] These catalysts are composed of equimolar quantities of sterically hindered Lewis acids-bases, a.k.a. frustrated Lewis pairs (FLP), as introduced by Stephan.…”
Section: Introductionmentioning
confidence: 99%
“…15 Only recently were highly selective metal-free catalysts for alkyne hydrogenation reported. 6,[16][17][18][19][20] These catalysts are composed of equimolar quantities of sterically hindered Lewis acids-bases, a.k.a. frustrated Lewis pairs (FLP), as introduced by Stephan.…”
Section: Introductionmentioning
confidence: 99%
“…[14] In the reaction of 7c-Et 4 N + with 14 b,t he resulting boron enolate 17-Et 4 N + (d( 11 B) = À3.0 ppm) could even be isolated and fully characterized. [15] To examine the potential of the N and s N values of 7a-c (Table 2) to predict the scope of reactions with electron-poor C=Cd ouble bonds,w em easured the kinetics of their reactions with several Michael acceptors and iminium ions of known electrophilicity E. [16] As shown in Table 3, the k 2 values of the reactions of the triarylborohydride 7c with the quinone methides 12 b,c and the iminium ions 18 a,b are in good agreement with the rate constants calculated from the tabulated electrophilicities E [16] and from the N and s N values of 7a-c (Table 2) obtained from Equation (1). In contrast, the measured k 2 values of the reactions with the Michael acceptors 14 a-c are 50-200 times lower than predicted, which is slightly outside the confidence range of Equation (1) (factor 10-100).…”
mentioning
confidence: 97%
“…Experimental details, compounds characterization, copies of 1 H, 13 C, 19 F NMR spectra, X-ray data, and details of DFT calculations.…”
Section: Supporting Informationmentioning
confidence: 99%