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Synthesis 2018; 50(11): 2211-2220
DOI: 10.1055/s-0036-1591968
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© Georg Thieme Verlag Stuttgart · New York

Iridium-Catalyzed Regioselective Borylation of Substituted Biaryls

Soneela Asghar
a   Department 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
a   Department 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
b   King 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
b   King 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
c   King Abdullah University of Science and Technology (KAUST), Core Labs, Thuwal, 23955-6900, Saudi Arabia
,
Rahman S. Z. Saleem
a   Department 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
a   Department 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*
a   Department 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
› Author AffiliationsWe thank Lahore University of Management Sciences for providing generous financial support for this research through start-up grant and faculty initiative fund to GAC. We also thank Higher Education Commission (HEC) of Pakistan for financial support through grant number NRPU-5903.
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Publication History

Received: 08 February 2018

Accepted after revision: 05 March 2018

Publication Date:
28 March 2018 (online)

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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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    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591968.
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