- Visible-Light-Driven Synthesis of Arylstannanes from Arylazo Sulfones
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The visible-light-driven preparation of (hetero)aryl stannanes was carried out under both photocatalyst- and metal-free conditions via irradiation of arylazo sulfones in the presence of hexaalkyldistannanes. The reaction shows a high efficiency and a wide substrates scope. The resulting crude organotin derivatives can be directly employed in a Stille protocol.
- Lian, Chang,Yue, Guanglu,Mao, Jinshan,Liu, Danyang,Ding, Yi,Liu, Zerong,Qiu, Di,Zhao, Xia,Lu, Kui,Fagnoni, Maurizio,Protti, Stefano
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supporting information
p. 5187 - 5191
(2019/07/03)
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- Synthesis of aryl trimethylstannanes from aryl amines: A sandmeyer-type stannylation reaction
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Sandmeyer-type stannylation: Stille coupling is one of the most powerful coupling reactions for C-C bond formation, whereas there are only limited methods to access aryl stannane compounds. A mild stannylation process based on a Sandmeyer-type transformation using aromatic amines as the starting materials is described. DCE: 1,2-dichloroethane. Copyright
- Qiu, Di,Meng, He,Jin, Liang,Wang, Shuai,Tang, Shengbo,Wang, Xi,Mo, Fanyang,Zhang, Yan,Wang, Jianbo
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supporting information
p. 11581 - 11584
(2013/11/06)
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- Organosilicon compounds. XLVII. The substituent effects and leaving group abilities of mono-, bis- and tris-(trimethylsilyl)silyl groups in electrophilic aromatic substitution
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The rates of cleavage at 50° by a mixture of ethanol (5 vol) and aqueous perchloric acid (2 vol) of the aryl-SnMe3 bonds of p-[(Me3Si)xMe(3-x)Si]C6H4SnMe3 compounds relative to that of phenyltrimethylstannane have been found to be 0.93 (x = 0), 1.31 (x = 1), 1.67 (x = 2) and 1.76 (x = 3). The increase in rate with the increasing magnitude of x can be attributed to inductive and hyperconjugative electron release from the SiSi bonds. The rates of cleavage at 50° by a mixture of methanol (5 vol) and aqueous perchloric acid (2 vol) of the aryl-Si bonds of the compounds [(Me3Si)xMe(3-x)Si]Ph are 1.0 (x = 0), 2.1 (x = 1), 0.35 (x = 2), and 0.056 (x = 3). The reactivity sequence as x is increased is attributed to opposition between a rate enhancement associated with the increasing electron release and a rate retardation associated with increasing steric hindrance, especially hindrance to solvation of the transition state.
- Cook,Eaborn,Walton
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