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 journalArticlepeer-review

6 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. (Figure presented.).

Original languageEnglish
Pages (from-to)3831-3836
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume359
Issue number21
DOIs
Publication statusPublished - 2017 Nov 10

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF-20100020209 and NRF-2015R1D1 A1 A01057200). C.-H.C. also thanks for a financial support from an NRF grant funded by the Korean Government (NRF-2014-011165, Center for New Directions in Organic Synthesis).

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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