A tautomerized ligand enabled meta selective C–H borylation of phenol

Saikat Guria, Mirja Md Mahamudul Hassan, Jiawei Ma, Sayan Dey, Yong Liang () and Buddhadeb Chattopadhyay ()
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Saikat Guria: Centre of Biomedical Research
Mirja Md Mahamudul Hassan: Centre of Biomedical Research
Jiawei Ma: Nanjing University
Sayan Dey: Centre of Biomedical Research
Yong Liang: Nanjing University
Buddhadeb Chattopadhyay: Centre of Biomedical Research

Nature Communications, 2023, vol. 14, issue 1, 1-11

Abstract: Abstract Remote meta selective C–H functionalization of aromatic compounds remains a challenging problem in chemical synthesis. Here, we report an iridium catalyst bearing a bidentate pyridine-pyridone (PY-PYRI) ligand framework that efficiently catalyzes this meta selective borylation reaction. We demonstrate that the developed concept can be employed to introduce a boron functionality at the remote meta position of phenols, phenol containing bioactive and drug molecules, which was an extraordinary challenge. Moreover, we have demonstrated that the method can also be applied for the remote C6 borylation of indole derivatives including tryptophan that was the key synthetic precursor for the total synthesis of Verruculogen and Fumitremorgin A alkaloids. The inspiration of this catalytic concept was started from the O–Si secondary interaction, which by means of several more detailed control experiments and detailed computational investigations revealed that an unprecedented Bpin shift occurs during the transformation of iridium bis(boryl) complex to iridium tris(boryl) complex, which eventually control the remote meta selectivity by means of the dispersion between the designed ligand and steering silane group.

Date: 2023
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DOI: 10.1038/s41467-023-42310-6

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