Publicaciones > Abengozar et al

Org Lett. 2018 Aug 17;20(16):4902-4906. doi: 10.1021/acs.orglett.8b02040. PubMed 30070487

C-H Functionalization of BN-Aromatics Promoted by Addition of Organolithium Compounds to the Boron Atom.

Alberto Abengozar¹, Miguel Angel Fernandez-Gonzalez², David Sucunza¹, Luis Manuel Frutos², Antonio Salgado³, Patricia Garcia-Garcia¹, Juan J Vaquero¹

1. Departamento de Quimica Organica y Quimica Inorganica, Instituto de Investigacion Quimica "Andres M. del Rio" (IQAR) , Universidad de Alcala , 28805 Alcala de Henares , Madrid , Spain.  2. Departamento de Quimica Analitica, Quimica Fisica e Ingenieria Quimica, Instituto de Investigacion Quimica "Andres M. del Rio" (IQAR) , Universidad de Alcala , 28805 Alcala de Henares , Madrid , Spain.  3. Centro de Espectroscopia de Resonancia Magnetica Nuclear (CERMN), CAI Quimicas , Universidad de Alcala , 28805 Alcala de Henares , Madrid , Spain.

Abstract

Addition of an organolithium compound to a BN-phenanthrene with embedded B and N atoms is proposed to result in coordination of RLi to the boron atom. This coordination, supported by NMR spectroscopy and DFT calculations, increases the nucleophilicity of the system in the beta position to the N atom and is therefore a useful tool for promoting regioselective C-H functionalization of BN aromatics.

Publicaciones > Abengozar et al

Chem Commun (Camb). 2018 Mar 6;54(20):2467-2470. doi: 10.1039/c7cc09264d. PubMed 29319090

Synthesis of functionalized helical BN-benzo[c]phenanthrenes.

Alberto Abengozar^a, Patricia Garcia-Garcia, David Sucunza, Adrian Perez-Redondo, Juan J Vaquero

Departamento de Quimica Organica y Quimica Inorganica, Instituto de Investigacion Quimica "Andres M. del Rio" (IQAR), Universidad de Alcala, 28805-Alcala de Henares, Madrid, Spain.

a. patricia.garciagarci@uah.es, juanjose.vaquero@uah.es

Abstract

A novel parent BN-benzo[c]phenanthrene, with helical chirality and remarkable structural features, has been easily obtained in three steps with a global yield of 55%. Moreover, Cl-substituted derivatives have been prepared and these have served as useful starting materials for the development of palladium-catalyzed cross-coupling reactions.

Publicaciones > Abengozar et al

Org Lett. 2017 Jul 7;19(13):3458-3461. doi: 10.1021/acs.orglett.7b01435. PubMed 28605913

Synthesis, Optical Properties, and Regioselective Functionalization of 4a-Aza-10a-boraphenanthrene.

Alberto Abengozar¹, Patricia Garcia-Garcia¹, David Sucunza¹, Luis Manuel Frutos², Obis Castano², Diego Sampedro³, Adrian Perez-Redondo¹, Juan J Vaquero¹

1. Departamento de Quimica Organica y Quimica Inorganica, Universidad de Alcala , 28871 Alcala de Henares, Madrid, Spain.  2. Departamento de Quimica Analitica, Quimica Fisica e Ingenieria Quimica, Universidad de Alcala , 28871 Alcala de Henares, Madrid, Spain.  3. Departamento de Quimica, Centro de Investigacion en Sintesis Quimica (CISQ), Universidad de La Rioja , Madre de Dios 53, 26006 Logrono, Spain.

Abstract

4a-Aza-10a-boraphenanthrene has been synthesized in only four steps from commercially available materials with a remarkable overall yield of 62%. In contrast to other BN-isosteres of phenathrene, this isomer is weakly fluorescent, which has been explained by means of computational studies that found a low energy conical intersection for the nonradiative deactivation of the excited state. Moreover, a completely regioselective functionalization of 4a-aza-10a-boraphenanthrene at C-1 by reaction with activated electrophiles has been achieved.