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Synlett 2022; 33(12): 1108-1116
DOI: 10.1055/a-1743-4650
DOI: 10.1055/a-1743-4650
synpacts
Electrostatically Directed meta-Selective Borylation of Arenes
This work was supported by the Science and Engineering Research Board, Science and Technology Award for Research (SERB-STAR, STR/2019/000045), the Science and Engineering Research Board, Core Research Grant (SERB-CRG, CRG/2018/000133), and the Science and Engineering Research Board, Scientific and Useful Profound Research Advancement (SERB-SUPRA, SPR/2019/000158). JC thanks University Grants Commission (UGC) for senior research fellowship (SRF), CH thanks the Council for Scientific and Industrial Research (CSIR) for senior research fellowship (SRF). BC thanks to the SERB for Science and Technology Award for Research. We also thank the Centre of Biomedical Research (CBMR) for research facilities.
Abstract
The constitutional challenge of an electrostatically directed meta borylation of sterically biased and unbiased substrates is summarized in the present work. The borylation follows an electrostatic interaction between the partially positive and negative charges of the ligand and substrate, respectively. Using our developed strategy, it has been demonstrated that a wide range of challenging substrates, especially 4-substituted substrates can be borylated at the meta position with excellent selectivity. Moreover, unsubstituted substrates are also displayed excellent meta selectivity. The reaction employs bench-stable ligand, proceeds at moderate reaction temperature (40–80 °C), precluding the need to synthesize bulky and sophisticated ligand/template.
Key words
C–H activation - meta borylation - iridium catalyst - aniline - electrostatic interaction - triflate - methanesulfonyl - acetyl - trifluoroacetylPublication History
Received: 29 December 2021
Accepted after revision: 18 January 2021
Accepted Manuscript online:
18 January 2022
Article published online:
15 February 2022
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