Intramolecular cyclopropanation and C-H insertion reactions with metal carbenoids generated from cyclopropenes

Accounts of Chemical Research
Alexis ArchambeauJanine Cossy

Abstract

Activation of unsaturated carbon-carbon bonds by means of transition metal catalysts is an exceptionally active research field in organic synthesis. In this context, due to their high ring strain, cyclopropenes constitute an interesting class of substrates that displays a versatile reactivity in the presence of transition metal catalysts. Metal complexes of vinyl carbenes are involved as key intermediates in a wide variety of transition metal-catalyzed ring-opening reactions of cyclopropenes. Most of the reported transformations rely on intermolecular or intramolecular addition of nucleophiles to these latter reactive species. This Account focuses specifically on the reactivity of carbenoids resulting from the ring-opening of cyclopropenes in cyclopropanation and C-H insertion reactions, which are arguably two of the most representative transformations of metal complexes of carbenes. Compared with the more conventional α-diazo carbonyl compounds, the use of cyclopropenes as precursors of metal carbenoids in intramolecular cyclopropanation or C-H insertion reactions has been largely underexploited. One of the challenges is to devise appropriately substituted and readily available cyclopropenes that would not only undergo regiose...Continue Reading

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Citations

Dec 25, 2015·Journal of the American Chemical Society·Qing-Qing ChengMichael P Doyle
Aug 11, 2016·Organic Letters·Trandon A BenderMichel R Gagné
Jun 17, 2016·Angewandte Chemie·Minqiang Jia, Shengming Ma
Mar 19, 2016·Chemistry : a European Journal·Alexis ArchambeauJanine Cossy
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Jul 18, 2015·Chemical Communications : Chem Comm·Yongming DengMichael P Doyle
Jun 24, 2017·Organic Letters·Lingheng KongXingwei Li
May 14, 2016·Chemical Communications : Chem Comm·Peng-Long ZhuMin Shi
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Oct 5, 2017·Chemistry : a European Journal·Florian F MulksA Stephen K Hashmi
Apr 20, 2019·Chemistry : a European Journal·Xiang YinAntonio M Echavarren
Jul 7, 2019·Angewandte Chemie·Jie ChenTeck-Peng Loh
Oct 17, 2019·Chemistry : a European Journal·Uyen P N TranRené M Koenigs
May 15, 2020·Chemical Communications : Chem Comm·Penghua LiMin Shi
Aug 26, 2015·Angewandte Chemie·María J GonzálezRubén Vicente
Aug 28, 2015·Chemistry : a European Journal·Yun LinYu Rao
Nov 7, 2019·Chemical Communications : Chem Comm·Melanie A DrewChristopher J T Hyland
May 8, 2018·Chemical Science·Ji Chen, Jimmy Wu
Jan 21, 2020·Chemical Society Reviews·Dong ZhuShifa Zhu
Jan 29, 2021·Organic & Biomolecular Chemistry·Sanjeev KumarVinaykumar Kanchupalli
Jan 16, 2021·Chemistry, an Asian Journal·Saiprasad NunewarVinaykumar Kanchupalli

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