Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis

Alexandra R. Rivero; Peter Fodran; Alica Ondrejkova; Carl-Johan Wallentin

doi:10.1021/acs.orglett.0c03058

Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis

Alexandra R. Rivero, Peter Fodran, Alica Ondrejkova, Carl-Johan Wallentin^*

^*Corresponding author for this work

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

30 Citations (Scopus)

Abstract

A mechanistically divergent method is described that, employing a commercially available hypervalent iodine(III) reagent, generates alkoxy radicals from 1 degrees, 2 degrees, and 3 degrees alcohols and allows their use in the functionalization of C(sp(3))-H and C(sp(2))-H bonds. This visible-light photoredox catalysis produces alkyl ethers via 1,5/6-hydrogen atom transfer or aryl ethers via 1,5-addition. This mild methodology provides a practical strategy for the synthesis of acetals, orthoesters, tetrahydrofurans, and chromanes.

Original language	English
Pages (from-to)	8436-8440
Number of pages	5
Journal	Organic letters
Volume	22
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.0c03058
Publication status	Published - 6-Nov-2020
Externally published	Yes

Keywords

STEREOSELECTIVE-SYNTHESIS
HYDROGEN-ATOM
ARYL ETHERS
FUNCTIONALIZATION
CYCLIZATION
OXIDATION
RING

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title = "Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis",

abstract = "A mechanistically divergent method is described that, employing a commercially available hypervalent iodine(III) reagent, generates alkoxy radicals from 1 degrees, 2 degrees, and 3 degrees alcohols and allows their use in the functionalization of C(sp(3))-H and C(sp(2))-H bonds. This visible-light photoredox catalysis produces alkyl ethers via 1,5/6-hydrogen atom transfer or aryl ethers via 1,5-addition. This mild methodology provides a practical strategy for the synthesis of acetals, orthoesters, tetrahydrofurans, and chromanes.",

keywords = "STEREOSELECTIVE-SYNTHESIS, HYDROGEN-ATOM, ARYL ETHERS, FUNCTIONALIZATION, CYCLIZATION, OXIDATION, RING",

author = "Rivero, {Alexandra R.} and Peter Fodran and Alica Ondrejkova and Carl-Johan Wallentin",

year = "2020",

month = nov,

day = "6",

doi = "10.1021/acs.orglett.0c03058",

language = "English",

volume = "22",

pages = "8436--8440",

journal = "Organic letters",

issn = "1523-7060",

publisher = "AMER CHEMICAL SOC INC",

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TY - JOUR

T1 - Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis

AU - Rivero, Alexandra R.

AU - Fodran, Peter

AU - Ondrejkova, Alica

AU - Wallentin, Carl-Johan

PY - 2020/11/6

Y1 - 2020/11/6

N2 - A mechanistically divergent method is described that, employing a commercially available hypervalent iodine(III) reagent, generates alkoxy radicals from 1 degrees, 2 degrees, and 3 degrees alcohols and allows their use in the functionalization of C(sp(3))-H and C(sp(2))-H bonds. This visible-light photoredox catalysis produces alkyl ethers via 1,5/6-hydrogen atom transfer or aryl ethers via 1,5-addition. This mild methodology provides a practical strategy for the synthesis of acetals, orthoesters, tetrahydrofurans, and chromanes.

AB - A mechanistically divergent method is described that, employing a commercially available hypervalent iodine(III) reagent, generates alkoxy radicals from 1 degrees, 2 degrees, and 3 degrees alcohols and allows their use in the functionalization of C(sp(3))-H and C(sp(2))-H bonds. This visible-light photoredox catalysis produces alkyl ethers via 1,5/6-hydrogen atom transfer or aryl ethers via 1,5-addition. This mild methodology provides a practical strategy for the synthesis of acetals, orthoesters, tetrahydrofurans, and chromanes.

KW - STEREOSELECTIVE-SYNTHESIS

KW - HYDROGEN-ATOM

KW - ARYL ETHERS

KW - FUNCTIONALIZATION

KW - CYCLIZATION

KW - OXIDATION

KW - RING

U2 - 10.1021/acs.orglett.0c03058

DO - 10.1021/acs.orglett.0c03058

M3 - Article

SN - 1523-7060

VL - 22

SP - 8436

EP - 8440

JO - Organic letters

JF - Organic letters

IS - 21

ER -

Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis

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Keywords

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