Iridium-Catalyzed Regioselective Borylation of Substituted Biaryls

Soneela Asghar; Tayyaba Shahzadi; Meshari Alazmi; Xin Gao; Abdul-Hamid Emwas; Rahman S. Z. Saleem; Farhat Batool; Ghayoor A. Chotana

doi:10.1055/s-0036-1591968

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(11): 2211-2220
DOI: 10.1055/s-0036-1591968

paper

Iridium-Catalyzed Regioselective Borylation of Substituted Biaryls

Soneela Asghar

^aDepartment of Chemistry & Chemical Engineering, Syed Babar Ali School of Science & Engineering, Lahore University of Management Sciences, Lahore 54792, Pakistan eMail: ghayoor.abbas@lums.edu.pk

,

Tayyaba Shahzadi

^aDepartment of Chemistry & Chemical Engineering, Syed Babar Ali School of Science & Engineering, Lahore University of Management Sciences, Lahore 54792, Pakistan eMail: ghayoor.abbas@lums.edu.pk

,

Meshari Alazmi

^bKing Abdullah University of Science and Technology (KAUST), Computational Bioscience Research Center (CBRC), Computer, Electrical and Mathematical Sciences and Engineering (CEMSE) Division, Thuwal, 23955-6900, Saudi Arabia

,

Xin Gao

^bKing Abdullah University of Science and Technology (KAUST), Computational Bioscience Research Center (CBRC), Computer, Electrical and Mathematical Sciences and Engineering (CEMSE) Division, Thuwal, 23955-6900, Saudi Arabia

,

Abdul-Hamid Emwas

^cKing Abdullah University of Science and Technology (KAUST), Core Labs, Thuwal, 23955-6900, Saudi Arabia

,

Rahman S. Z. Saleem

^aDepartment of Chemistry & Chemical Engineering, Syed Babar Ali School of Science & Engineering, Lahore University of Management Sciences, Lahore 54792, Pakistan eMail: ghayoor.abbas@lums.edu.pk

,

Farhat Batool

^aDepartment of Chemistry & Chemical Engineering, Syed Babar Ali School of Science & Engineering, Lahore University of Management Sciences, Lahore 54792, Pakistan eMail: ghayoor.abbas@lums.edu.pk

,

Ghayoor A. Chotana*

^aDepartment of Chemistry & Chemical Engineering, Syed Babar Ali School of Science & Engineering, Lahore University of Management Sciences, Lahore 54792, Pakistan eMail: ghayoor.abbas@lums.edu.pk

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Abstract

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Abstract

Biarylboronic esters are generally prepared by directed ortho-metalation or by Miyaura borylation and hence rely on the presence of a directing group or pre-functionalization. In this paper, the preparation of biarylboronic esters by direct C–H borylation of biaryl substrates is reported. Sterically governed regioselectivities were observed in the borylation of appropriately substituted biaryls by using [Ir(OMe)(COD)]₂ precatalyst and di-tert-butylbipyridyl ligand. The resulting biarylboronic esters were isolated in 38–98% yields. The synthesized biarylboronic esters were further successfully employed in C–O, C–Br, and C–C coupling reactions.

Key words

biaryls - boronic esters - iridium-catalyzed - borylation - regioselective - sterically governed - Suzuki coupling

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