Transfer of organic groups to gold using organotin compounds

Meyer, Nadine Sabra; Sivanathan, Sivatharushan; Mohr, Fabian

doi:10.1016/j.jorganchem.2010.10.060

Cited by 22 publications

(19 citation statements)

References 29 publications

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“…There are only very few reports of isolated transmetalations from tin to gold and vice versa. The transmetalation of Ar groups from SnArMe 3 (Ar=Ph, naphtyl, or 8‐iodonaphtyl) to [AuCl(EPh 3 )] (E=P, As) complexes has been reported, whereas the same reaction fails with SnPh( n Bu) 3 13. Attempts at performing Ar transmetalations with SnAr 4 or SnClAr 3 (Ar=C 6 F 5 , C 6 F 3 Cl 2 , C 6 Cl 5 ) were also unsuccessful 14.…”

Section: Methodsmentioning

confidence: 99%

Stille Coupling Involving Bulky Groups Feasible with Gold Cocatalyst

et al. 2013

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Section: Methodsmentioning

confidence: 99%

Stille Coupling Involving Bulky Groups Feasible with Gold Cocatalyst

et al. 2013

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“…The covalent bond pathway connecting iodine and tin in (8-iodo-1-naphthyl)trimethyltin (refcode AQIVUS) [123] is reminiscent of that connecting bromine and tin in VEKKUT, and this translates into a supramolecular similarity between the C-Sn···I TB in the former compound and the Cl-Sn···Br TB in the latter. In the crystal structure of bromo(4-iodo-1,2,3,4-tetraphenyl-1,3-butadienyl)diphenyltin (refcode SICSOM) (Fig.…”

Section: Halogen Atoms As Tetrel Bond Acceptorsmentioning

confidence: 99%

Close contacts involving germanium and tin in crystal structures: experimental evidence of tetrel bonds

et al. 2018

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Modeling indicates the presence of a region of low electronic density (a Bσ-hole^) on group 14 elements, and this offers an explanation for the ability of these elements to act as electrophilic sites and to form attractive interactions with nucleophiles. While many papers have described theoretical investigations of interactions involving carbon and silicon, such investigations of the heavier group 14 elements are relatively scarce. The purpose of this review is to rectify, to some extent, the current lack of experimental data on interactions formed by germanium and tin with nucleophiles. A survey of crystal structures in the Cambridge Structural Database is reported. This survey reveals that close contacts between Ge or Sn and lone-pair-possessing atoms are quite common, they can be either intra-or intermolecular contacts, and they are usually oriented along the extension of the covalent bond formed by the tetrel with the most electron-withdrawing substituent. Several examples are discussed in which germanium and tin atoms bear four carbon residues or in which halogen, oxygen, sulfur, or nitrogen substituents replace one, two, or three of those carbon residues. These close contacts are assumed to be the result of attractive interactions between the involved atoms and afford experimental evidence of the ability of germanium and tin to act as electrophilic sites, namely tetrel bond (TB) donors. This ability can govern the conformations and the packing of organic derivatives in the solid state. TBs can therefore be considered a promising and robust tool for crystal engineering.

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“…Initial attempts to transfer the 1,1′‐ferrocenediyl group to a gold(I) centre using the tin(IV) compound [Fe(η 5 ‐C 5 H 4 SnMe 3 ) 2 ] as transmetallation reagent, which we had previously developed for this purpose, were unsuccessful , . However, the reaction of ferroceneboronic acid with various gold–phosphine compounds in the presence of base afforded multimetallic complexes [FcAu(PPh 3 )] ( 1 ) and [(µ‐P‐P)(AuFc) 2 ] {P‐P = dppe ( 2 ), dppf ( 3 )}, in high yields as air‐stable orange compounds (Scheme ).…”

Section: Resultsmentioning

confidence: 99%