A β-Diketiminate-Stabilized Sila-Acyl Chloride: Systematic Access to Base-Stabilized Silicon Analogues of Classical Carbonyl Compounds

Angewandte Chemie
Dinh Cao Huan DoSimon Aldridge

Abstract

An oxidation/substitution strategy for the synthesis of silicon analogues of classical organic carbonyl compounds is reported, by making use of a novel β-diketiminate-supported sila-acyl chloride-the first example of such a compound isolated without the use of a stabilizing Lewis acid. Nucleophilic substitution at the SiIV center allows direct access to the corresponding sila-aldehyde and sila-ester. An alternative approach utilizing the reverse order of synthetic steps is thwarted by the facile rearrangement of the corresponding SiII systems featuring either H or OR substituents. As such, the isolation of (N-nacnac)Si(O)Cl represents a key step forward in enabling the synthesis of sila-carbonyl compounds by a synthetic approach ubiquitous in organic chemistry.

References

May 4, 2006·Angewandte Chemie·Cheuk-Wai SoRainer B Oswald
Jul 27, 2006·Journal of the American Chemical Society·Matthias DriessDieter Lentz
May 19, 2007·Journal of the American Chemical Society·Shenglai YaoMatthias Driess
May 14, 2009·Journal of the American Chemical Society·Yun XiongMatthias Driess
Jan 16, 2010·Chemistry : a European Journal·Alexander C FilippouGregor Schnakenburg
Aug 3, 2010·Angewandte Chemie·David GauAntoine Baceiredo
Sep 9, 2011·Journal of the American Chemical Society·Takako MuraokaKeiji Ueno
Oct 18, 2011·Journal of the American Chemical Society·Rajendra S GhadwalGernot Frenking
Jul 13, 2012·Chemical Communications : Chem Comm·Rajendra S GhadwalGernot Frenking
Apr 10, 2013·Angewandte Chemie·Ricardo RodriguezTsuyoshi Kato
Nov 30, 2013·Angewandte Chemie·Alexander C FilippouGregor Schnakenburg
Jun 30, 2015·Journal of the American Chemical Society·Yuzhong WangGregory H Robinson
Jun 30, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Clément Camp, John Arnold
Mar 2, 2017·Angewandte Chemie·Ricardo RodriguezTsuyoshi Kato
Jul 4, 2017·Angewandte Chemie·Isabel Alvarado-BeltranTsuyoshi Kato
Jan 30, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Yun XiongMatthias Driess

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Citations

Nov 18, 2018·Chemistry : a European Journal·Debotra SarkarShigeyoshi Inoue
May 17, 2019·Angewandte Chemie·Ryo KobayashiTakeaki Iwamoto
May 14, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Dominik ReiterShigeyoshi Inoue
Aug 20, 2020·Chemical Society Reviews·Changkai ShanMatthias Driess
Jun 20, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Dinh Cao Huan DoSimon Aldridge
May 6, 2019·Chemistry : a European Journal·Taichi KoikeTakeaki Iwamoto
Mar 27, 2020·Chemical Communications : Chem Comm·Dinh Cao Huan DoSimon Aldridge
Jul 15, 2020·Angewandte Chemie·Ying Kai Loh, Simon Aldridge
Aug 7, 2020·Chemistry : a European Journal·Catherine Weetman
Jan 13, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Ryo KobayashiTakeaki Iwamoto
Jun 2, 2021·Angewandte Chemie·Hanqiang WangZuowei Xie
Dec 15, 2020·Journal of the American Chemical Society·Tobias HeitkemperChristian P Sindlinger
Jul 30, 2019·Journal of the American Chemical Society·Dominik ReiterShigeyoshi Inoue
Sep 14, 2019·Inorganic Chemistry·L Carina SiemesFelicitas Lips

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