Electronically-driven regioselective iridium-catalyzed C-H borylation of donor-π-acceptor chromophores containing triarylboron acceptors

Chemistry : a European Journal
Florian RauchTodd B Marder

Abstract

We observed a surprisingly high electronically-driven regioselectivity for the iridium-catalyzed C-H borylation of donor-π-acceptor (D-π-A) systems with diphenylamino ( 1 ) or carbazolyl ( 2 ) moieties as the donor, bis(2,6-bis(trifluoromethyl)phenyl)boryl ( B( F Xyl) 2 ) as the acceptor, and 1,4-phenylene as the π-bridge. Under our conditions, borylation was observed only at the sterically least encumbered para-positions of the acceptor group. As boronate esters are versatile building blocks for organic synthesis (C-C coupling, functional group transformations) the C-H borylation represents a simple potential method for post-functionalization by which electronic or other properties of D-π-A systems can be fine-tuned for specific applications. The photophysical and electrochemical properties of the borylated ( 1-(Bpin) 2 ) and unborylated ( 1 ) diphenylamino-substituted D-π-A systems were investigated. Interestingly, the borylated derivative exhibits coordination of THF to the boronate ester moieties, influencing the photophysical properties and exemplifying the non-innocence of boronate esters.

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Citations

Feb 18, 2021·Chemical Reviews·Ya-Ming TianTodd B Marder
Jun 25, 2021·Chemical Science·Jiang HeTodd B Marder

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Methods Mentioned

BETA
column chromatography
NMR
X‐ray

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