2019
DOI: 10.1002/anie.201910060
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Orthogonal Nanoparticle Catalysis with Organogermanes

Abstract: Although nanoparticles are widely used as catalysts, little is knownabout their potential ability to trigger privileged transformations as compared to homogeneous molecular or bulk heterogeneous catalysts.W eh erein demonstrate (and rationalize) that nanoparticles displayorthogonal reactivity to molecular catalysts in the cross-coupling of aryl halides with aryl germanes.W hile the aryl germanes are unreactive in L n Pd 0 /L n Pd II catalysis and allowselective functionalization of established coupling partner… Show more

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Cited by 96 publications
(77 citation statements)
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“…This feature allows for the construction of multiply halogenated scaffolds for diverse synthetic purposes. Even sterically demanding o,o-disubstituted (20 and 21)a nd heterocyclic scaffolds (22)(23)(24)(25), whose boronic acid derivatives show ah igh tendencyt od ecompose, [15] underwent halogenation in high yields.E specially pleasing is the selective halogenation of 3-thiophenyl substrates (23 and 25), as the 2thiophenyl-position is the more nucleophilic site and hence usually preferentially targeted in reactions with electrophiles.…”
Section: Angewandte Chemiementioning
confidence: 99%
See 1 more Smart Citation
“…This feature allows for the construction of multiply halogenated scaffolds for diverse synthetic purposes. Even sterically demanding o,o-disubstituted (20 and 21)a nd heterocyclic scaffolds (22)(23)(24)(25), whose boronic acid derivatives show ah igh tendencyt od ecompose, [15] underwent halogenation in high yields.E specially pleasing is the selective halogenation of 3-thiophenyl substrates (23 and 25), as the 2thiophenyl-position is the more nucleophilic site and hence usually preferentially targeted in reactions with electrophiles.…”
Section: Angewandte Chemiementioning
confidence: 99%
“…As such, there is an eed for an ew and orthogonal functional group,a nd we targeted the trialkyl germanium functionality.T his nontoxic [21] class of reagents offers high stability against moisture,a ir,a cids and bases, [22b] and has shown promise in reactions with molecular halogens. [19] We recently uncovered that aryl germanes displayed privileged and orthogonal reactivities in metal catalysis over alternative functionalities, [22,23] and therefore envisioned that potentially orthogonal halogenations might also be feasible,which might unleash access to selective multi-halogenation of molecules.…”
Section: Introductionmentioning
confidence: 99%
“…Ihr Forschungsprogramm ist an der Schnittstelle von organischer Synthese, mechanistischer und rechnergestützter Chemie angesiedelt, mit einem besonderen Schwerpunkt auf homogener Metallkatalyse. Schoenebeck, die bereits mit ihrem Autoren‐Profil vorgestellt wurde, berichtete kürzlich über orthogonale Nanopartikelkatalyse mit Organogermanen und über die selektive Diversifizierung polyhalogenierter Arylfluorsulfate…”
Section: Vorgestellt …unclassified
“…As a frequent Angewandte Chemie author, Schoenebeck has already been featured with her Author Profile . Recently her group has published original contributions in this journal on orthogonal nanoparticle catalysis with organogermanes and on the selective diversification of polyhalogenated aryl fluorosulfates…”
Section: Featured …mentioning
confidence: 99%