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Abstract
Benzoxaborinines are intermediates en-route to bicyclic boronates that are important active pharmaceutical ingredients (APIs). Herein, the haloboration of o-alkynyl-phenols using BX3 (X = Cl or Br) is disclosed as a route to form C4-X-benzoxaborinines with good functional group tolerance. Computational studies indicated that there are two similar in barrier mechanisms: (i) double alkyne haloboration followed by retro-haloboration; (ii) concerted trans-haloboration involving an exogenous chloride source. The C4-halide in these benzoxaborinines is useful, with a one-pot haloboration-Negishi cross coupling protocol effective to form benzoxaborinines with an alkyl or an aryl at C4. Therefore this method is a useful addition to the toolbox for synthesizing bicyclic-boronates that are attracting increasing attention as APIs.
Original language | English |
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Journal | Angewandte Chemie International Edition |
Early online date | 1 Mar 2023 |
DOIs | |
Publication status | E-pub ahead of print - 1 Mar 2023 |
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Dive into the research topics of 'Haloboration of o‐Alkynyl Phenols Generates Halogenated Bicyclic‐Boronates'. Together they form a unique fingerprint.Projects
- 1 Finished
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Enabling Catalytic Cross Couplings with only Zinc Electrophiles, Nucleophiles and Boranes
Ingleson, M. (Principal Investigator)
1/04/19 → 31/12/23
Project: Research