One-pot, three-step synthesis of cyclopropylboronic acid pinacol esters from synthetically tractable propargylic silyl ethers

Jonathan A. Spencer, Craig Jamieson, Eric P. A. Talbot

Research output: Contribution to journalArticle

11 Citations (Scopus)
36 Downloads (Pure)

Abstract

Simple propargylic silyl ethers can be converted to complex cyclopropylboronic acid pinacol esters in an efficient onepot procedure. Terminal acetylenes undergo a Schwartz’s reagent catalyzed hydroboration; subsequent addition of further Schwartz’s reagent and Lewis acid-mediated activation of neighboring silyl ether allows cyclization to access a range of cyclopropylboronic acid pinacol esters. The scope includes aromatic, aliphatic, quaternary, and spiro substituted cyclopropyl rings, which can be transformed via Suzuki coupling into a range of lead-like substituted cyclopropyl aryl products.
Original languageEnglish
Number of pages4
JournalOrganic Letters
Early online date6 Jul 2017
DOIs
Publication statusE-pub ahead of print - 6 Jul 2017

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Ethers
esters
ethers
Esters
Lewis Acids
acids
Acids
Alkynes
reagents
Cyclization
synthesis
hydroboration
Ether
Chemical activation
acetylene
activation
rings
products
Lead

Keywords

  • Suzuki coupling
  • cyclopropyl aryl
  • propargylic silyl ether

Cite this

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title = "One-pot, three-step synthesis of cyclopropylboronic acid pinacol esters from synthetically tractable propargylic silyl ethers",
abstract = "Simple propargylic silyl ethers can be converted to complex cyclopropylboronic acid pinacol esters in an efficient onepot procedure. Terminal acetylenes undergo a Schwartz’s reagent catalyzed hydroboration; subsequent addition of further Schwartz’s reagent and Lewis acid-mediated activation of neighboring silyl ether allows cyclization to access a range of cyclopropylboronic acid pinacol esters. The scope includes aromatic, aliphatic, quaternary, and spiro substituted cyclopropyl rings, which can be transformed via Suzuki coupling into a range of lead-like substituted cyclopropyl aryl products.",
keywords = "Suzuki coupling, cyclopropyl aryl, propargylic silyl ether",
author = "Spencer, {Jonathan A.} and Craig Jamieson and Talbot, {Eric P. A.}",
year = "2017",
month = "7",
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doi = "10.1021/acs.orglett.7b01778",
language = "English",
journal = "Organic Letters",
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publisher = "American Chemical Society",

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One-pot, three-step synthesis of cyclopropylboronic acid pinacol esters from synthetically tractable propargylic silyl ethers. / Spencer, Jonathan A.; Jamieson, Craig; Talbot, Eric P. A. .

In: Organic Letters, 06.07.2017.

Research output: Contribution to journalArticle

TY - JOUR

T1 - One-pot, three-step synthesis of cyclopropylboronic acid pinacol esters from synthetically tractable propargylic silyl ethers

AU - Spencer, Jonathan A.

AU - Jamieson, Craig

AU - Talbot, Eric P. A.

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AB - Simple propargylic silyl ethers can be converted to complex cyclopropylboronic acid pinacol esters in an efficient onepot procedure. Terminal acetylenes undergo a Schwartz’s reagent catalyzed hydroboration; subsequent addition of further Schwartz’s reagent and Lewis acid-mediated activation of neighboring silyl ether allows cyclization to access a range of cyclopropylboronic acid pinacol esters. The scope includes aromatic, aliphatic, quaternary, and spiro substituted cyclopropyl rings, which can be transformed via Suzuki coupling into a range of lead-like substituted cyclopropyl aryl products.

KW - Suzuki coupling

KW - cyclopropyl aryl

KW - propargylic silyl ether

UR - http://pubs.acs.org/doi/abs/10.1021/acs.orglett.7b01778

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