Producción Científica Profesorado

Preparation of symmetrical C2-C2-linked bis- and tris-6-bromoindoles by Sonogashira couplings and 5-endo-dig cyclization induced by nBu4NF.



Alvarez Hernandez, Alejandro

2016

Raúl Balderrama-Martínez-Sotomayor, Mariana Flores-Jarillo, Alejandro Alvarez-Hernandez. Preparation of symmetrical C2-C2-linked bis- and tris-6-bromoindoles by Sonogashira couplings and 5-endo-dig cyclization induced by nBu4NF. ARKIVOC, 2016 ,(iii), 36-47http://quod.lib.umich.edu/a/ark/5550190.p009.319/1


Abstract


Preparation of symmetrical C2-C2 linked bis-6-bromoindoles and one tris-6-bromoindole containing ether spacers is described. Double regioselective Sonogashira coupling at the C-I bond of benzyl (5-bromo-2-iodophenyl)carbamate with dialkynes allowed preparation of the corresponding bis-benzyl(2-alkynyl-5-bromo)carbamates. Tetrabutylammonium fluoride (TBAF) promoted 5-endo-dig cyclization was successful with substrates derived from alkyldialkynes but failed with substrates derived from aryldialkynes as base catalysis was not sufficient to promote nucleophilic attack on these electron rich alkynes.



Producto de Investigación




Artículos relacionados

Aroylthioureas: new organic ionophores for heavy-metal ion selective electrodes

An efficient potassium cyanide-promoted synthesis of 2-arylbenzoxazoles from [4.3.0]boron heterobicy...

Phenylboronic acid catalyzed-cyanide promoted, one-pot synthesis of 2-(2-hydroxyphenyl)benzoxazole d...

Et3B, an Efficient Mediator for Xanthate Transfer Based Radical Processes

Enantioselective synthesis of ?-amino acids. Part 10: Preparation of novel ?,?- and ?,?-disubstitute...

Et3, and efficient Mediator for Xanthate Transfer Based Radical Processes.

Synthesis and Study of Monomeric and Dimeric Boronates by Spectroscopic Methods and X-ray Crystallog...

r-Alkylation of (S)-Asparagine with Self-Regeneration of the Stereogenic Center: Enantioselective Sy...

Phenylboronic acid catalyzed-cyanide promoted, one-pot synthesis of 2-(2-hydroxyphenyl)benzoxazole d...

Synthesis and Study of Isomeric Benzo[1,4]oxazines and Benzothiazolines by NMR Spectroscopy and X-Ra...