A β-Carbon elimination strategy for convenient in situ access to cyclopentadienyl metal complexes

Chemical Science
G SmitsN Cramer

Abstract

The electronic and steric properties of tailored cyclopentadienyl (Cp) ligands are powerful handles to modulate the catalytic properties of their metal complexes. This requires the individual preparation, purification and storage of each ligand/metal combination. Alternative, ideally in situ, complexation protocols would be of high utility. We disclose a new approach to access Cp metal complexes. Common metal precursors rapidly react with cyclopentadienyl carbinols via β-carbon eliminations to directly give the Cp-metal complexes. An advantage of this is the direct and flexible use of storable pre-ligands. No auxiliary base is required and the Cp complexes can be prepared in situ in the reaction vessel for subsequent catalytic transformations.

References

Oct 28, 1996·Physical Review Letters·J P PerdewM Ernzerhof
Oct 18, 2001·Journal of the American Chemical Society·Y TeraoM Nomura
May 27, 2004·Journal of the American Chemical Society·Brenton DeBoefDalibor Sames
Mar 9, 2006·Journal of the American Chemical Society·Pinjing ZhaoJohn F Hartwig
Mar 22, 2007·Journal of the American Chemical Society·Masayuki IwasakiKoichiro Oshima
Jan 12, 2008·Accounts of Chemical Research·Yan Zhao, Donald G Truhlar
Jan 12, 2008·Angewandte Chemie·Ryo ShintaniTamio Hayashi
Mar 30, 2010·Journal of the American Chemical Society·Tobias Seiser, Nicolai Cramer
Oct 19, 2010·Chemical Communications : Chem Comm·Masahiro Murakami, Takanori Matsuda
Feb 2, 2011·The Journal of Chemical Physics·Stephan N Steinmann, Clemence Corminboeuf
Jun 18, 2011·Chimia·Stephan N Steinmann, Clémence Corminboeuf
Aug 31, 2011·Journal of the American Chemical Society·Hu LiZhang-Jie Shi
Oct 12, 2011·Chemical Communications : Chem Comm·Todd K Hyster, Tomislav Rovis
Jan 12, 2012·Chemical Communications : Chem Comm·Naoki IshidaMasahiro Murakami
Oct 10, 2012·Journal of the American Chemical Society·Naoki IshidaMasahiro Murakami
Jan 5, 2013·Journal of the American Chemical Society·Baihua Ye, Nicolai Cramer
Aug 19, 2014·Journal of the American Chemical Society·Guoyong SongZhaomin Hou
Dec 23, 2014·Chemical Communications : Chem Comm·Naoki IshidaMasahiro Murakami
Apr 18, 2015·Accounts of Chemical Research·Baihua Ye, Nicolai Cramer
Jul 15, 2015·Journal of the American Chemical Society·Fedor Romanov-MichailidisTomislav Rovis
Sep 17, 2015·Journal of the American Chemical Society·David Kossler, Nicolai Cramer
Nov 8, 2011·Journal of Chemical Theory and Computation·Stephan N Steinmann, Clemence Corminboeuf
Jul 13, 2010·Journal of Chemical Theory and Computation·Stephan N Steinmann, Clemence Corminboeuf
Feb 11, 2016·Journal of the American Chemical Society·Christopher G NewtonNicolai Cramer

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Citations

Feb 22, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Angela E E WandlerStefan Bräse
Jun 8, 2018·Chemistry : a European Journal·Kui Fun LeeGuochen Jia
Jan 30, 2020·Chemistry : a European Journal·Tatsuhiko YoshinoShigeki Matsunaga
Jul 17, 2020·Angewandte Chemie·Josep Mas-RosellóNicolai Cramer
Sep 9, 2020·Chemical Reviews·Łukasz WoźniakNicolai Cramer
Mar 23, 2019·Journal of the American Chemical Society·Kristers OzolsNicolai Cramer
Jan 25, 2018·Organic Letters·Shogo KamoKazunori Tsubaki
May 23, 2018·Journal of the American Chemical Society·Shunsuke OnoderaFumitoshi Kakiuchi

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Methods Mentioned

BETA
NMR

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