Palladium-catalyzed cross-coupling reactions of 2-indolyldimethylsilanols with substituted aryl halides

Organic Letters
Scott E Denmark, John D Baird

Abstract

[reaction: see text] A mild and general cross-coupling reaction of 2-indolylsilanols has been developed. The experimental variables that lead to successful coupling are (1) the use of sodium tert-butoxide as the activator, (2) the use of copper(I) iodide in stoichiometric quantities, and (3) the use of Pd2(dba)3.CHCl3 as the catalyst. Under these conditions N-(Boc)-2-indolyldimethylsilanol reacts with a variety of aromatic iodides to afford the coupling products in good yield (70-84%).

References

Jun 28, 2001·Journal of the American Chemical Society·S E Denmark, R F Sweis
Oct 25, 2001·The Journal of Organic Chemistry·Molly E. Mowery, Philip DeShong
Oct 12, 2002·The Journal of Organic Chemistry·Enrique VazquezJoseph F Payack
May 8, 2003·Journal of the American Chemical Society·Jae-Young Lee, Gregory C Fu
Jul 23, 2003·Current Medicinal Chemistry·Antonio Ramírez, Silvina García-Rubio
Nov 8, 2003·The Journal of Organic Chemistry·Scott E Denmark, Steven A Tymonko

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Citations

May 12, 2011·Chemical Reviews·Sandro Cacchi, Giancarlo Fabrizi
Jun 1, 2010·Journal of the American Chemical Society·Natalia ChernyakVladimir Gevorgyan
Nov 13, 2008·Journal of the American Chemical Society·Scott E Denmark, Nathan S Werner
Jan 22, 2008·The Journal of Organic Chemistry·Scott E DenmarkChristopher S Regens
Jun 22, 2011·Tetrahedron·Pingping Tang, Tobias Ritter
Oct 1, 2015·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Naoki Asao
May 11, 2011·Chemistry : a European Journal·Wei HanArmin R Ofial
Jan 27, 2012·Chemistry : a European Journal·Ken-ichi ShimizuAtsushi Satsuma
Jul 7, 2011·Angewandte Chemie·Jubi JohnEric Doris
Oct 20, 2015·Organic Process Research & Development·Scott E Denmark, Andrea Ambrosi
Feb 10, 2009·Journal of the American Chemical Society·Scott E DenmarkJoseck M Muhuhi
Mar 25, 2005·Organic Letters·Salih OzçubukçuCarsten Bolm
Mar 18, 2009·Journal of the American Chemical Society·Alvaro GordilloCarmen López-Mardomingo
Sep 7, 2012·Journal of the American Chemical Society·Hui Zhou, Christina Moberg
Oct 15, 2011·The Journal of Organic Chemistry·Kai ChengXian-Man Zhang
Sep 2, 2016·The Journal of Organic Chemistry·Tuo Xi, Zhan Lu
Feb 20, 2016·Chemistry : a European Journal·Juan delPozoPablo Espinet
Jul 5, 2007·Organic & Biomolecular Chemistry·Haruhiko Fuwa, Makoto Sasaki
May 8, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Xiaoming ZhangWanzhi Chen
Jul 22, 2009·Chemistry : a European Journal·Jessica R HerronZachary T Ball
Mar 25, 2010·Angewandte Chemie·Scott E Denmark, Jack H-C Liu
Mar 17, 2010·Angewandte Chemie·Oleg VechorkinXile Hu
Aug 18, 2010·Angewandte Chemie·Zhe Lu, Gregory C Fu
Jul 2, 2005·Angewandte Chemie·K C NicolaouDavid Sarlah
Dec 1, 2010·Israel Journal of Chemistry·Scott E Denmark, Jack H-C Liu
May 30, 2007·Pest Management Science·Uri Gerson, Phyllis G Weintraub
Nov 11, 2009·Chemistry : a European Journal·Anke SpurgSiegfried R Waldvogel
Nov 4, 2011·Chemical Society Reviews·Hannah F SoreDavid R Spring
Jul 12, 2013·Angewandte Chemie·Gregory L Beutner, Scott E Denmark

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