Chemoselective Deprotection of Symmetrically Diprotected Resorcinol N-Methyliminodiacetate (MIDA) Boronates Using the MIDA Boronate Moiety as a Blocking Group: Synthesis of Monoprotected Resorcinol MIDA Boronates

Se Jin Lee; Jooyeon Yoon; Sang Woo Han; Cheol Hong Cheon

doi:10.1021/acs.orglett.4c04027

Chemoselective Deprotection of Symmetrically Diprotected Resorcinol N-Methyliminodiacetate (MIDA) Boronates Using the MIDA Boronate Moiety as a Blocking Group: Synthesis of Monoprotected Resorcinol MIDA Boronates

Se Jin Lee, Jooyeon Yoon, Sang Woo Han, Cheol Hong Cheon^*

^*Corresponding author for this work

Department of Chemistry

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

1 Citation (Scopus)

Abstract

A novel protocol for the synthesis of monoprotected resorcinol N-methyliminodiacetate (MIDA) boronates was developed via the chemoselective deprotection of diprotected resorcinol MIDA derivatives with identical protecting groups, utilizing the MIDA boronate moiety as a blocking group for deprotection. This protocol exhibited a broad substrate scope, and the resulting MIDA boronates were readily isolated by simple filtration from the reaction mixture. Furthermore, the utility of this protocol was demonstrated by converting the resulting MIDA boronates into value-added chemicals containing resorcinol scaffolds.

Original language	English
Pages (from-to)	11117-11122
Number of pages	6
Journal	Organic Letters
Volume	26
Issue number	51
DOIs	https://doi.org/10.1021/acs.orglett.4c04027
Publication status	Published - 2024 Dec 27

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Publisher Copyright:
© 2024 American Chemical Society.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Chemoselective Deprotection of Symmetrically Diprotected Resorcinol N-Methyliminodiacetate (MIDA) Boronates Using the MIDA Boronate Moiety as a Blocking Group: Synthesis of Monoprotected Resorcinol MIDA Boronates. / Lee, Se Jin; Yoon, Jooyeon; Han, Sang Woo et al.
In: Organic Letters, Vol. 26, No. 51, 27.12.2024, p. 11117-11122.

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

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title = "Chemoselective Deprotection of Symmetrically Diprotected Resorcinol N-Methyliminodiacetate (MIDA) Boronates Using the MIDA Boronate Moiety as a Blocking Group: Synthesis of Monoprotected Resorcinol MIDA Boronates",

abstract = "A novel protocol for the synthesis of monoprotected resorcinol N-methyliminodiacetate (MIDA) boronates was developed via the chemoselective deprotection of diprotected resorcinol MIDA derivatives with identical protecting groups, utilizing the MIDA boronate moiety as a blocking group for deprotection. This protocol exhibited a broad substrate scope, and the resulting MIDA boronates were readily isolated by simple filtration from the reaction mixture. Furthermore, the utility of this protocol was demonstrated by converting the resulting MIDA boronates into value-added chemicals containing resorcinol scaffolds.",

author = "Lee, \{Se Jin\} and Jooyeon Yoon and Han, \{Sang Woo\} and Cheon, \{Cheol Hong\}",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

year = "2024",

month = dec,

day = "27",

doi = "10.1021/acs.orglett.4c04027",

language = "English",

volume = "26",

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T2 - Synthesis of Monoprotected Resorcinol MIDA Boronates

AU - Lee, Se Jin

AU - Yoon, Jooyeon

AU - Han, Sang Woo

AU - Cheon, Cheol Hong

PY - 2024/12/27

Y1 - 2024/12/27

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AB - A novel protocol for the synthesis of monoprotected resorcinol N-methyliminodiacetate (MIDA) boronates was developed via the chemoselective deprotection of diprotected resorcinol MIDA derivatives with identical protecting groups, utilizing the MIDA boronate moiety as a blocking group for deprotection. This protocol exhibited a broad substrate scope, and the resulting MIDA boronates were readily isolated by simple filtration from the reaction mixture. Furthermore, the utility of this protocol was demonstrated by converting the resulting MIDA boronates into value-added chemicals containing resorcinol scaffolds.

UR - https://www.scopus.com/pages/publications/85212792793

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JO - Organic Letters

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ER -

Chemoselective Deprotection of Symmetrically Diprotected Resorcinol N-Methyliminodiacetate (MIDA) Boronates Using the MIDA Boronate Moiety as a Blocking Group: Synthesis of Monoprotected Resorcinol MIDA Boronates

Abstract

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