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Iridium-catalyzed C–H borylation of pyridines

Sadler, S.A.; Tajuddin, H.; Mkhalid, I.A.I.; Batsanov, A.S.; Albesa-Jove, D.; Cheung, M.S.; Maxwell, A.C.; Shukla, L.; Roberts, B.; Blakemore, D.C.; Lin, Z.; Marder, T.B.; Steel, P.G.

Iridium-catalyzed C–H borylation of pyridines Thumbnail


S.A. Sadler

H. Tajuddin

I.A.I. Mkhalid

A.S. Batsanov

D. Albesa-Jove

M.S. Cheung

A.C. Maxwell

L. Shukla

B. Roberts

D.C. Blakemore

Z. Lin

T.B. Marder


The iridium-catalysed C–H borylation is a valuable and attractive method for the preparation of aryl and heteroaryl boronates. However, application of this methodology for the preparation of pyridyl and related azinyl boronates can be challenged by low reactivity and propensity for rapid protodeborylation, particularly for a boronate ester ortho to the azinyl nitrogen. Competition experiments have revealed that the low reactivity is due to inhibition of the active catalyst through coordination of the azinyl nitrogen lone pair at the vacant site on the iridium. This effect can be overcome through the incorporation of a substituent at C-2. Moreover, when this is sufficiently electron-withdrawing protodeborylation is sufficiently slowed to permit isolation and purification of the C-6 boronate ester. Following functionalization, reduction of the directing C-2 substituent provides the product arising from formal ortho borylation of an unhindered pyridine ring.


Sadler, S., Tajuddin, H., Mkhalid, I., Batsanov, A., Albesa-Jove, D., Cheung, M., …Steel, P. (2014). Iridium-catalyzed C–H borylation of pyridines. Organic and Biomolecular Chemistry, 12(37), 7318-7327.

Journal Article Type Article
Acceptance Date Aug 1, 2014
Online Publication Date Aug 1, 2014
Publication Date Oct 7, 2014
Deposit Date Sep 26, 2014
Publicly Available Date Sep 30, 2014
Journal Organic and Biomolecular Chemistry
Print ISSN 1477-0520
Electronic ISSN 1477-0539
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 12
Issue 37
Pages 7318-7327


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