Bridge heteroarylation of bicyclo[1.1.1]pentane derivatives

Joseph M. Anderson; Nicholas D. Measom; John A. Murphy; Darren L. Poole

doi:10.1021/acs.orglett.3c00412

Bridge heteroarylation of bicyclo[1.1.1]pentane derivatives

Joseph M. Anderson, Nicholas D. Measom, John A. Murphy, Darren L. Poole

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17 Citations (Scopus)

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Abstract

Herein, we report the decarboxylative Minisci heteroarylation of bicyclo[1.1.1]pentane (BCP) and 2-oxabicyclo[2.1.1]hexane (oBCH) derivatives at the bridge positions. In an operationally simple, photocatalyst-free process, free bridge carboxylic acids are directly coupled with nonprefunctionalized heteroarenes to provide rare examples of polysubstituted BCP and oBCH derivatives in synthetically useful yields. Additionally, the impact of the BCP core on the physicochemical properties of a representative example compared to those of its all-aromatic ortho- and meta-substituted analogues is evaluated.

Original language	English
Pages (from-to)	2053–2057
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	12
Early online date	17 Mar 2023
DOIs	https://doi.org/10.1021/acs.orglett.3c00412
Publication status	Published - 31 Mar 2023

Keywords

bridge heteroarylation
bicyclo[1.1.1]pentane derivatives

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10.1021/acs.orglett.3c00412

Anderson-etal-OL-2023-Bridge-heteroarylation-of-bicyclo-1-1-1-pentane-derivativesAccepted author manuscript, 444 KBLicence: Strath_1

Cite this

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title = "Bridge heteroarylation of bicyclo[1.1.1]pentane derivatives",

abstract = "Herein, we report the decarboxylative Minisci heteroarylation of bicyclo[1.1.1]pentane (BCP) and 2-oxabicyclo[2.1.1]hexane (oBCH) derivatives at the bridge positions. In an operationally simple, photocatalyst-free process, free bridge carboxylic acids are directly coupled with nonprefunctionalized heteroarenes to provide rare examples of polysubstituted BCP and oBCH derivatives in synthetically useful yields. Additionally, the impact of the BCP core on the physicochemical properties of a representative example compared to those of its all-aromatic ortho- and meta-substituted analogues is evaluated.",

keywords = "bridge heteroarylation, bicyclo[1.1.1]pentane derivatives",

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year = "2023",

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doi = "10.1021/acs.orglett.3c00412",

language = "English",

volume = "25",

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journal = "Organic Letters",

issn = "1523-7060",

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T1 - Bridge heteroarylation of bicyclo[1.1.1]pentane derivatives

AU - Anderson, Joseph M.

AU - Measom, Nicholas D.

AU - Murphy, John A.

AU - Poole, Darren L.

PY - 2023/3/31

Y1 - 2023/3/31

N2 - Herein, we report the decarboxylative Minisci heteroarylation of bicyclo[1.1.1]pentane (BCP) and 2-oxabicyclo[2.1.1]hexane (oBCH) derivatives at the bridge positions. In an operationally simple, photocatalyst-free process, free bridge carboxylic acids are directly coupled with nonprefunctionalized heteroarenes to provide rare examples of polysubstituted BCP and oBCH derivatives in synthetically useful yields. Additionally, the impact of the BCP core on the physicochemical properties of a representative example compared to those of its all-aromatic ortho- and meta-substituted analogues is evaluated.

AB - Herein, we report the decarboxylative Minisci heteroarylation of bicyclo[1.1.1]pentane (BCP) and 2-oxabicyclo[2.1.1]hexane (oBCH) derivatives at the bridge positions. In an operationally simple, photocatalyst-free process, free bridge carboxylic acids are directly coupled with nonprefunctionalized heteroarenes to provide rare examples of polysubstituted BCP and oBCH derivatives in synthetically useful yields. Additionally, the impact of the BCP core on the physicochemical properties of a representative example compared to those of its all-aromatic ortho- and meta-substituted analogues is evaluated.

KW - bridge heteroarylation

KW - bicyclo[1.1.1]pentane derivatives

UR - https://pubs.acs.org/page/orlef7/about.html

U2 - 10.1021/acs.orglett.3c00412

DO - 10.1021/acs.orglett.3c00412

M3 - Article

SN - 1523-7060

VL - 25

SP - 2053

EP - 2057

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Bridge heteroarylation of bicyclo[1.1.1]pentane derivatives

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Bridge heteroarylation of bicyclo[1.1.1]pentane derivatives

Abstract

Keywords

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PP: Accelerated Discovery and Development of New Medicines: Prosperity Partnership for a Healthier Nation

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