Efficient access to titanaaziridines by C-H activation of N-methylanilines at ambient temperature

Angewandte Chemie
Manfred ManßenRüdiger Beckhaus

Abstract

Titanaaziridines or η(2)-imine titanium complexes are considered key intermediates of the titanium-catalyzed hydroaminoalkylation of alkenes. Herein, we present an efficient synthetic route to this class of compounds, starting from N-methylanilines and a bis(η(5):η(1)-pentafulvene)titanium complex. Consecutive reactions on the η(2)-methyleneaniline complexes, characterized for the first time, prove a high chemical versatility. In particular, hydroaminoalkylation products were found in reactions of the three-membered titanacycles with alkenes. For the first time, all the intermediates of the hydroaminoalkylation of alkenes were isolated and characterized.

References

May 14, 2009·Angewandte Chemie·Peter W Roesky
Feb 27, 2010·Angewandte Chemie·Wolfgang SchererPeter W Roesky
Mar 4, 2010·Angewandte Chemie·Raphael KubiakSven Doye
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Aug 14, 2012·Angewandte Chemie·Junichiro YamaguchiKenichiro Itami
Sep 13, 2014·Angewandte Chemie·Huw M L Davies, Daniel Morton

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Citations

Apr 27, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·David ArmstrongUlrich Fekl
Feb 9, 2016·Chemistry : a European Journal·Manfred ManßenRüdiger Beckhaus
May 23, 2017·Acta Crystallographica. Section E, Crystallographic Communications·Tim OswaldRüdiger Beckhaus
Sep 16, 2017·Chemistry : a European Journal·Manfred ManßenRüdiger Beckhaus
Dec 5, 2019·Chemistry : a European Journal·Michael RosienSven Doye
Aug 28, 2020·Chemical Society Reviews·Manfred Manßen, Laurel L Schafer
Aug 28, 2020·Chemistry : a European Journal·Tobias KaperSven Doye
Dec 19, 2017·Acta Crystallographica. Section E, Crystallographic Communications·Malte FischerRüdiger Beckhaus
Dec 24, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Malte FischerRuediger Beckhaus
Jul 10, 2020·Chemistry : a European Journal·Michael Warsitz, Sven Doye
Jan 23, 2021·Chemistry : a European Journal·Tobias KaperSven Doye
Apr 10, 2015·Inorganic Chemistry·Malte SietzenJoachim Ballmann
Dec 1, 2020·Journal of the American Chemical Society·Erick Nuñez BahenaLaurel L Schafer
Feb 6, 2017·Chemical Reviews·Preethanuj PreethalayamK V Radhakrishnan

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