Preparation of Building Blocks for Iterative Suzuki-Miyaura Reactions via Direct Bromination of Aryl Boronic Acids: One-Pot Total Syntheses of Dictyoterphenyls A and B

Chun Young Lee, Cheol-Hong Cheon

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

A highly efficient method for the preparation of 4-alkoxy-3-bromophenyl boronic acid N-methyliminodiacetic acid (MIDA) esters as building blocks in iterative Suzuki-Miyaura reactions from the 4-alkoxyphenylboronic acids is described using a boronic acid moiety as a blocking group in bromination reactions. With these MIDA boronates, the total syntheses of dictyoterphenyls A and B were developed in only two separate one-pot operations. Furthermore, we have developed a more practical protocol for the preparation of meta-terphenyl natural products by simply adding the second aryl halide and water to the reaction mixture via the controlled release technique.

Original languageEnglish
JournalAdvanced Synthesis and Catalysis
DOIs
Publication statusAccepted/In press - 2017

Fingerprint

Boronic Acids
Acids
Biological Products
Esters
Water
N-methyliminodiacetic acid
alkoxyl radical

Keywords

  • Blocking Group
  • Dictyoterphenyls A and B
  • Iterative Suzuki-Miyaura reaction
  • MIDA Boronates
  • Pot-economy

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

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abstract = "A highly efficient method for the preparation of 4-alkoxy-3-bromophenyl boronic acid N-methyliminodiacetic acid (MIDA) esters as building blocks in iterative Suzuki-Miyaura reactions from the 4-alkoxyphenylboronic acids is described using a boronic acid moiety as a blocking group in bromination reactions. With these MIDA boronates, the total syntheses of dictyoterphenyls A and B were developed in only two separate one-pot operations. Furthermore, we have developed a more practical protocol for the preparation of meta-terphenyl natural products by simply adding the second aryl halide and water to the reaction mixture via the controlled release technique.",
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AU - Cheon, Cheol-Hong

PY - 2017

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AB - A highly efficient method for the preparation of 4-alkoxy-3-bromophenyl boronic acid N-methyliminodiacetic acid (MIDA) esters as building blocks in iterative Suzuki-Miyaura reactions from the 4-alkoxyphenylboronic acids is described using a boronic acid moiety as a blocking group in bromination reactions. With these MIDA boronates, the total syntheses of dictyoterphenyls A and B were developed in only two separate one-pot operations. Furthermore, we have developed a more practical protocol for the preparation of meta-terphenyl natural products by simply adding the second aryl halide and water to the reaction mixture via the controlled release technique.

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