Arylboronic acids and arylpinacolboronate esters in Suzuki coupling reactions involving indoles. Partner role swapping and heterocycle protection

The Journal of Organic Chemistry
Mònica PrietoErnest Giralt

Abstract

Yields of Suzuki couplings involving indoles depended upon (i) whether arylboronic acids or arylpinacolboronate esters were used, (ii) whether the heterocycle was the aryl halide or the arylboron coupling partner, and (iii) whether the heterocycle was protected or not. Highest yields, which were unaffected by incorporating Boc or Tos protection at the heterocyclic nitrogen, were obtained when indole bromides were reacted with phenylboronic acids. When indolylboronic acids were reacted with phenyl bromides, yields were somewhat lower and depended on the nitrogen substituent, being highest in the absence of protection, lower in the presence of the Boc group, and lowest of all with the Tos group. Arylpinacolboronate esters were less reactive than arylboronic acids. They required considerably longer reaction times and furnished generally lower yields of biaryl. Furthermore, irrespective of whether the heterocycle was the aryl bromide or the arylpinacolboronate ester, these yields were highest when it was protected with the Tos group. Yields were lower with the Boc group, and unprotected heterocycles gave only traces of biaryl. Careful selection of arylboron reagent, of coupling partner roles, and of protecting groups are essential ...Continue Reading

References

May 18, 2000·Accounts of Chemical Research·C Amatore, A Jutand
Sep 20, 2001·Combinatorial Chemistry & High Throughput Screening·J ToisJ Taskinen
Oct 24, 2001·The Journal of Organic Chemistry·Karl Matos, John A. Soderquist
May 9, 2002·Chemical Reviews·Jwanro HassanMarc Lemaire
Jun 12, 2002·Bioorganic & Medicinal Chemistry·Stefan BräseKerstin Knepper
Apr 26, 2003·The Journal of Organic Chemistry·Lei ZhuMingbao Zhang

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Citations

May 12, 2011·Chemical Reviews·Sandro Cacchi, Giancarlo Fabrizi
Apr 12, 2013·Journal of Medicinal Chemistry·Charles M KeyariPhilippe Diaz
Sep 9, 2010·Chemical & Pharmaceutical Bulletin·Hideyuki KonishiKei Manabe
Feb 9, 2016·Journal of the American Chemical Society·Paulo H S PaiotiAaron Aponick
Apr 18, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Antonella MiglioriniMaria Antonietta Loreto
Nov 28, 2017·Organic & Biomolecular Chemistry·Monika TomanováPetr Cankař
Apr 28, 2006·Angewandte Chemie·Kelvin L BillingsleyStephen L Buchwald
Jan 25, 2007·ChemMedChem·Verónica F V PrazeresConcepción González-Bello
Mar 28, 2008·Chemistry : a European Journal·Christoph A Fleckenstein, Herbert Plenio
Apr 1, 2011·Hormone Molecular Biology and Clinical Investigation·Štefan StarčevićTea Lanišnik Rižner
Dec 25, 2008·The Journal of Organic Chemistry·Gary A MolanderLauren E Kennedy
Jul 14, 2005·Chemical Reviews·Sandro Cacchi, Giancarlo Fabrizi
Feb 11, 2015·Journal of Medicinal Chemistry·Simon KleebBeat Ernst
Aug 6, 2013·Journal of the American Chemical Society·M Alexander DüfertStephen L Buchwald
Dec 7, 2006·Journal of the American Chemical Society·Sulagna PaulMilton R Smith
Dec 16, 2006·The Journal of Organic Chemistry·Gary A Molander, Adam R Brown
Mar 12, 2005·The Journal of Organic Chemistry·Maria AlfonsiFabio Marinelli
Jan 29, 2011·Bioorganic & Medicinal Chemistry·Eduard DolušićRaphaël Frédérick

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