N-Pyridylimidates as Traceless Acyl Equivalents for Directed C-O Bond Functionalization

Steven J. Underwood; Christopher J. Douglas

doi:10.1021/acs.orglett.2c03961

N-Pyridylimidates as Traceless Acyl Equivalents for Directed C-O Bond Functionalization

Steven J. Underwood
, Christopher J. Douglas

Chemistry (Twin Cities)

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

4 Scopus citations

Abstract

Directing groups are a common strategy to target traditionally inert bonds, with an easily removable directing group being ideal. Herein we disclose our method for rhodium-catalyzed C-O bond functionalization of N-pyridylimidates using a recyclable and traceless amine directing group. In addition to the substrate scope, we discuss the behavior of this class of compounds and how that behavior affects their reactivity.

Original language	English (US)
Pages (from-to)	146-151
Number of pages	6
Journal	Organic Letters
Volume	25
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.2c03961
State	Published - Jan 13 2023

Bibliographical note

Funding Information:
We thank Aaron Reynolds (UMN) for assistance with X-ray crystallography. We thank Profs. Erin Carlson and Steve Kass (UMN) and Carolyn Anderson (Calvin University) for insightful discussions. We thank the Office for the Vice President of Research, University of Minnesota (Grant No. 573872), for partially funding this work.

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© 2022 American Chemical Society.

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title = "N-Pyridylimidates as Traceless Acyl Equivalents for Directed C-O Bond Functionalization",

abstract = "Directing groups are a common strategy to target traditionally inert bonds, with an easily removable directing group being ideal. Herein we disclose our method for rhodium-catalyzed C-O bond functionalization of N-pyridylimidates using a recyclable and traceless amine directing group. In addition to the substrate scope, we discuss the behavior of this class of compounds and how that behavior affects their reactivity.",

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doi = "10.1021/acs.orglett.2c03961",

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T1 - N-Pyridylimidates as Traceless Acyl Equivalents for Directed C-O Bond Functionalization

AU - Underwood, Steven J.

AU - Douglas, Christopher J.

N1 - Funding Information: We thank Aaron Reynolds (UMN) for assistance with X-ray crystallography. We thank Profs. Erin Carlson and Steve Kass (UMN) and Carolyn Anderson (Calvin University) for insightful discussions. We thank the Office for the Vice President of Research, University of Minnesota (Grant No. 573872), for partially funding this work. Publisher Copyright: © 2022 American Chemical Society.

PY - 2023/1/13

Y1 - 2023/1/13

N2 - Directing groups are a common strategy to target traditionally inert bonds, with an easily removable directing group being ideal. Herein we disclose our method for rhodium-catalyzed C-O bond functionalization of N-pyridylimidates using a recyclable and traceless amine directing group. In addition to the substrate scope, we discuss the behavior of this class of compounds and how that behavior affects their reactivity.

AB - Directing groups are a common strategy to target traditionally inert bonds, with an easily removable directing group being ideal. Herein we disclose our method for rhodium-catalyzed C-O bond functionalization of N-pyridylimidates using a recyclable and traceless amine directing group. In addition to the substrate scope, we discuss the behavior of this class of compounds and how that behavior affects their reactivity.

UR - https://www.scopus.com/pages/publications/85145444891

UR - https://www.scopus.com/pages/publications/85145444891#tab=citedBy

U2 - 10.1021/acs.orglett.2c03961

DO - 10.1021/acs.orglett.2c03961

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AN - SCOPUS:85145444891

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SP - 146

EP - 151

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

N-Pyridylimidates as Traceless Acyl Equivalents for Directed C-O Bond Functionalization

Abstract

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