A general method for interconversion of boronic acid protecting groups: Trifluoroborates as common intermediates

Quentin I. Churches; Joel F. Hooper; Craig A. Hutton

doi:10.1021/acs.joc.5b00182

A general method for interconversion of boronic acid protecting groups: Trifluoroborates as common intermediates

Quentin I. Churches, Joel F. Hooper, Craig A. Hutton

Research output: Contribution to journal › Article › Research › peer-review

35 Citations (Scopus)

Abstract

We have developed a general protocol for the interconversion of diverse protected boronic acids, via intermediate organotrifluoroborates. N-Methyliminodiacetyl boronates, which have been hitherto resistant to direct conversion to trifluoroborates, have been shown to undergo fluorolysis at elevated temperatures. Subsequent solvolysis of organotrifluoroborates in the presence of trimethylsilyl chloride and a wide range of bis-nucleophiles enables the generation of a variety of protected boronic acids.

Original language	English
Pages (from-to)	5428-5435
Number of pages	8
Journal	The Journal of Organic Chemistry
Volume	80
Issue number	11
DOIs	https://doi.org/10.1021/acs.joc.5b00182
Publication status	Published - 5 Jun 2015
Externally published	Yes

Keywords

Boron
MIDA boronates
Acids

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10.1021/acs.joc.5b00182

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abstract = "We have developed a general protocol for the interconversion of diverse protected boronic acids, via intermediate organotrifluoroborates. N-Methyliminodiacetyl boronates, which have been hitherto resistant to direct conversion to trifluoroborates, have been shown to undergo fluorolysis at elevated temperatures. Subsequent solvolysis of organotrifluoroborates in the presence of trimethylsilyl chloride and a wide range of bis-nucleophiles enables the generation of a variety of protected boronic acids.",

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T2 - Trifluoroborates as common intermediates

AU - Churches, Quentin I.

AU - Hooper, Joel F.

AU - Hutton, Craig A.

PY - 2015/6/5

Y1 - 2015/6/5

N2 - We have developed a general protocol for the interconversion of diverse protected boronic acids, via intermediate organotrifluoroborates. N-Methyliminodiacetyl boronates, which have been hitherto resistant to direct conversion to trifluoroborates, have been shown to undergo fluorolysis at elevated temperatures. Subsequent solvolysis of organotrifluoroborates in the presence of trimethylsilyl chloride and a wide range of bis-nucleophiles enables the generation of a variety of protected boronic acids.

AB - We have developed a general protocol for the interconversion of diverse protected boronic acids, via intermediate organotrifluoroborates. N-Methyliminodiacetyl boronates, which have been hitherto resistant to direct conversion to trifluoroborates, have been shown to undergo fluorolysis at elevated temperatures. Subsequent solvolysis of organotrifluoroborates in the presence of trimethylsilyl chloride and a wide range of bis-nucleophiles enables the generation of a variety of protected boronic acids.

KW - Boron

KW - MIDA boronates

KW - Acids

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U2 - 10.1021/acs.joc.5b00182

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JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

SN - 0022-3263

IS - 11

ER -

A general method for interconversion of boronic acid protecting groups: Trifluoroborates as common intermediates

Abstract

Keywords

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