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. 2020 Jul 15;142(28):11988-11992.
doi: 10.1021/jacs.0c04159. Epub 2020 Jul 2.

Arylphosphonate-Directed Ortho C-H Borylation: Rapid Entry into Highly-Substituted Phosphoarenes

Feiyang Xu  1   2 , Olivia M Duke  1 , Daniel Rojas  1 , Hanka M Eichelberger  1   2 , Raphael S Kim  1 , Timothy B Clark  2 , Donald A Watson  1
Affiliations

Arylphosphonate-Directed Ortho C-H Borylation: Rapid Entry into Highly-Substituted Phosphoarenes

Feiyang Xu et al. J Am Chem Soc. .

Abstract

Phosphonate-directed ortho C-H borylation of aromatic phosphonates is reported. Using simple starting materials and commercially accessible catalysts, this method provides steady access to o-phosphonate arylboronic esters bearing pendant functionality and flexible substitution patterns. These products serve as flexible precursors for a variety of highly substituted phosphoarenes, and in situ downstream functionalization of the products is described.

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Figures

Figure 1.
Figure 1.
Previous Synthesis of Ortho-Boryl Aryl Phosphonates and Our Design.
Scheme 1.
Scheme 1.
Scope of Phosphonate-Directed C–H Borylation
Scheme 2.
Scheme 2.
In Situ Downstream Functionalization
Scheme 3.
Scheme 3.
Biaryl Phosphonate Synthesis and Their Utility in Ligand Synthesis
Scheme 4.
Scheme 4.
Comparison Between Phosphonate and Ester
See this image and copyright information in PMC

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