- 3-Silaazetidine: An Unexplored yet Versatile Organosilane Species for Ring Expansion toward Silaazacycles
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Small-ring silacycles are important organosilane species in main-group chemistry and have found numerous applications in organic synthesis. 3-Silaazetidine, a unique small silacycle bearing silicon and nitrogen atoms, has not been adequately explored due to the lack of a general synthetic scheme and its sensitivity to air. Here, we describe that 3-silaazetidine can be easily prepared in situ from diverse air-stable precursors (RSO2NHCH2SiR12CH2Cl). 3-Silaazetidine shows excellent functional group tolerance in a palladium-catalyzed ring expansion reaction with terminal alkynes, giving 3-silatetrahydropyridines and diverse silaazacycle derivatives, which are promising ring frameworks for the discovery of Si-containing functional molecules.
- Dong, Xue,Gao, Lu,He, Yuanhang,Li, Linjie,Song, Zhenlei,Wang, Qiantao,Wang, Wanshu,Zhou, Song
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supporting information
p. 11141 - 11151
(2021/08/03)
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- Anionic access to silylated and germylated binuclear heterocycles
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A simple access to silylated and germylated binuclear heterocycles, based on an original anionic rearrangement, is described. A set of electron-rich and electron-poor silylated aromatic and heteroaromatic substrates were tested to understand the mechanism and the factors controlling this rearrangement, in particular its regioselectivity. This parameter was shown to follow the rules proposed before from a few examples. Then, the effect of the substituents borne by the silicon itself, in particular the selectivity of the ligand transfer, was studied. Additionally, this chemistry was extended to germylated substrates. A hypervalent germanium species, comparable to the putative intermediate proposed with silicon, seems to be involved. However, a pathway implicating the elimination of LiCH2Cl was observed for the first time with this element, leading to unexpected products of the benzo-oxa (or benzo-aza) germol-type.
- Boddaert, Thomas,Francois, Cyril,Mistico, Laetitia,Querolle, Olivier,Meerpoel, Lieven,Angibaud, Patrick,Durandetti, Muriel,Maddaluno, Jacques
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supporting information
p. 10131 - 10139
(2014/08/18)
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Various prochirals silapropan-diols were synthetised with good yields. Several enzymatic-catalysed hydrolyses or transesterification have been attempted on this products; when we change the parameters: as the temperature in transesterification reaction, t
- Djerourou, Abdel Hafid,Blanco, Luis
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p. 107 - 136
(2007/10/03)
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- Synthesis of optically active 2-sila-1,3-propanediols derivatives by enzymatic transesterification
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Lipase from Candida cylindracea and lipase from Chromobacterium viscosum allowed the synthesis of silyl-chiral optically active compounds by mono-transesterification of 2-sila-1,3-propanediols.
- Djerourou,Blanco
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p. 6325 - 6326
(2007/10/02)
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