Reactivity of a N→Sn Coordinated Distannyne: Reduction and Hydrogen Abstraction

Bouška, Marek; Tydlitát, Jiří; Jirásko, Robert; Růžička, Aleš; Dostál, Libor; Herres‐Pawlis, Sonja; Hoffmann, Alexander; Jambor, Roman

doi:10.1002/ejic.201800370

Cited by 12 publications

(3 citation statements)

References 57 publications

(43 reference statements)

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“…Hence, it is proposed that 6 reacts with (RCH 2 )SnCl 2 * to produce the diarylmethane and RCH 2 Sn(H)Cl 2 (path B in Scheme 4). [21] A second SnÀ C bond cleavage in Scheme 3. Synthesis of diarylmethanes from bis(arylmethyl)tin dichlorides and arenes.…”

Section: Chemistry-a European Journalmentioning

confidence: 99%

Temperature‐Assisted Generation of Arylmethyl Radicals from Bis(arylmethyl)tin Dichlorides: Efficient Reagents for − Bond‐Forming Reactions

Dhanwant

Saini

Chivers

et al. 2023

Chemistry A European J

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The oxidative-addition reaction between an arylmethyl chloride (RCH 2 Cl; R=1-C 10 H 7 , 2,4,6-Me 3 C 6 H 2 , 4-MeC 6 H 4 , 3-MeC 6 H 4 , C 6 H 5 , 4-ClC 6 H 4 ) and tin powder in boiling toluene produces bis(arylmethyl)tin dichlorides, [(RCH 2 ) 2 SnCl 2 ] in good yields. At 160 °C in mesitylene bis(1-naphthylmethyl)tin dichloride undergoes SnÀ C homolytic cleavage to generate two 1-naphthylmethyl radicals (1-C 10 H 7 CH 2 * ) which were trapped by TEMPO (C 9 H 8 NO * ). Subsequently, the radicals (RCH 2 * ) produced in this manner were utilized for efficient substitution reactions with electron-rich arenes (R'H; R' = 2,4,6-Me 3 C 6 H 2 , 1,2,4,5-Me 4 C 6 H, 1,2,3,4,5-Me 5 C 6 ) to obtain a variety of unsymmetrical diarylmethanes (RR'CH 2 ). The addition of one equivalent of iodine (I 2 ) to the reaction mixture resulted in a significant increase in the yields of coupled products.

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Section: Chemistry-a European Journalmentioning

confidence: 99%

Temperature‐Assisted Generation of Arylmethyl Radicals from Bis(arylmethyl)tin Dichlorides: Efficient Reagents for − Bond‐Forming Reactions

Dhanwant

Saini

Chivers

et al. 2023

Chemistry A European J

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“…[44] The redox potential of the tin atom in the diorganodistannyne L I SnSnL I [L I = 2,6-(R2NCH2)2C6H3, R = Me], [45] as well as the reduction ability of these type of distannynes were also studied. [46] The coordination ability of chlorostannylene 27 was tested towards different transition metal complexes, as show in Scheme 10. The Pd(II) atom in complexes 54, 55, 59 is in a square planar geometry, while the Sn atom adopts a trans trigonal bipyramidal geometry.…”

Section: Reactivity Of Stannylenesmentioning

confidence: 99%

“…[57] In a similar manner, chromium complex 88 was also obtained (Scheme 13). [46] Cr(CO)5SnCl2•THF was added to [2,6-(MeOCH2)2C6H3]Li to form stannylenepentacarbonylchromium complex 87. The structure of the complex is similar to that with tungsten (Scheme 13), the Sn-O distances are of 2.393(3) and 2.409(3) Å, suggesting strong interactions.…”

Section: No Datamentioning

confidence: 99%

The Role of Monoanionic Aryl Pincer Ligands in the Stabilization of Group 14 Metallylenes

2020

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Pincer ligands have an important role in stabilizing group 14 metallylenes. The particular structure of the aryl pincer ligands makes them a unique ligand platform. This review is focused on presenting monoanionic metallylenes stabilized by aryl pincer‐type ligands, described so far in the literature, with focus on their synthesis, structural features, and reactivity. Throughout this work, the close correlation between structure and reactivity is highlighted, as well as the manner in which this influences the stability of the compounds and their potential applications.

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Controlling Catenation in Germanium(I) Chemistry through Hemilability

et al. 2021

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We present anovel approach for constructing chains of Group 14 metal atoms linked by unsupported metal-metal bonds that exploits hemilabile ligands to generate unsaturated metal sites.T he formation/nature of catenated species (oligodimetallynes) can be controlled by the use of (acidic/basic) "protecting groups" and through variation of the ligand scaffold.Reduction of Ar NiPr2 GeCl (Ar NiPr2 = 2,6-( i Pr 2 NCH 2 ) 2 C 6 H 3 )-featuring hemilabile N i Pr 2 donors-yields (Ar NiPr2 Ge) 4 (2), which contains at etrameric Ge 4 chain. 2 represents an ovel type of al inear homo-catenated Ge I compound featuring unsupported E À Eb onds.T rapping experiments reveal that ak ey structural component is the central two-way Ge = Ge donor-acceptor bond:r eactions with IMe 4 and W(CO) 5 (NMe 3 )g ive the base-or acid-stabilized digermynes (Ar NiPr2 Ge(IMe 4 )) 2 ( 4)and (Ar NiPr2 Ge{W(CO) 5 }) 2 (5), respectively.The use of smaller N-donors leads to stronger Ge-N interactions and quenchingo fc atenation behaviour: reduction of Ar NEt2 GeCl gives the digermyne (Ar NEt2 Ge) 2 , while the unsymmetrical system Ar NEt2 GeGeAr NiPr2 dimerizes to give tetranuclear (Ar NEt2 GeGeAr NiPr2 ) 2 through aggregation at the N i Pr 2 -ligated Ge I centres.

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Reactivity of a N→Sn Coordinated Distannyne: Reduction and Hydrogen Abstraction

Cited by 12 publications

References 57 publications

Temperature‐Assisted Generation of Arylmethyl Radicals from Bis(arylmethyl)tin Dichlorides: Efficient Reagents for − Bond‐Forming Reactions

Temperature‐Assisted Generation of Arylmethyl Radicals from Bis(arylmethyl)tin Dichlorides: Efficient Reagents for − Bond‐Forming Reactions

The Role of Monoanionic Aryl Pincer Ligands in the Stabilization of Group 14 Metallylenes

Controlling Catenation in Germanium(I) Chemistry through Hemilability

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