Journal
SYNLETT
Volume 33, Issue 12, Pages 1108-1116Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/a-1743-4650
Keywords
C-H activation; meta borylation; iridium catalyst; aniline; electrostatic interaction; triflate; methanesulfonyl; acetyl; trifluoroacetyl
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Funding
- Science and Engineering Research Board, Science and Technology Award for Research (SERB-STAR) [STR/2019/000045]
- Science and Engineering Research Board, Core Research Grant (SERB-CRG) [CRG/2018/000133]
- Science and Engineering Research Board, Scientific and Useful Profound Research Advancement (SERB-SUPRA) [SPR/2019/000158]
- University Grants Commission (UGC)
- Council for Scientific and Industrial Research (CSIR)
- SERB
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This work summarizes the constitutional challenge of an electrostatically directed meta borylation reaction of sterically biased and unbiased substrates. Using a developed strategy, a wide range of challenging substrates can be selectively borylated at the meta position. Furthermore, the reaction proceeds at moderate temperature without the need for synthesizing complex ligand/templates.
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 degrees C), precluding the need to synthesize bulky and sophisticated ligand/template.
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