Photoinduced Deoxygenative Borylations of Aliphatic Alcohols

Jingjing Wu; Robin Baer; Lin Guo; Adam Noble; Varinder Kumar Aggarwal

doi:10.1002/anie.201910051

Photoinduced Deoxygenative Borylations of Aliphatic Alcohols

Jingjing Wu, Robin Baer, Lin Guo, Adam Noble, Varinder Kumar Aggarwal

School of Chemistry

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

120 Citations (Scopus)

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Abstract

A photochemical method for converting aliphatic alcohols into boronic esters is described. Preactivation of the alcohol as a 2‐iodophenyl‐thionocarbonate enables a novel Barton‐McCombie‐type radical deoxygenation that proceeds efficiently with visible light irradiation and without the requirement for a photocatalyst, a radical initiator, or tin or silicon hydrides. The resultant alkyl radical is intercepted by bis(catecholato)diboron, furnishing boronic esters from a diverse range of structurally complex alcohols.

Original language	English
Number of pages	6
Journal	Angewandte Chemie - International Edition
Early online date	15 Oct 2019
DOIs	https://doi.org/10.1002/anie.201910051
Publication status	E-pub ahead of print - 15 Oct 2019

Keywords

Boronsäureester
Borylierungen
Desoxygenierung
Photochemie
Radikalreaktionen

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10.1002/anie.201910051

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This is the author accepted manuscript (AAM). The final published version (version of record) is available online via Wiley at https://onlinelibrary.wiley.com/doi/10.1002/ange.201910051. Please refer to any applicable terms of use of the publisher.
Accepted author manuscript, 1.14 MB

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FRESCO: Efficient, Flexible Synthesis of Molecules with Tailored Shapes: from Photoswitchable Helices to anti-Cancer Compounds
Aggarwal, V. K. (Principal Investigator)
1/10/15 → 31/03/21
Project: Research

Cite this

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title = "Photoinduced Deoxygenative Borylations of Aliphatic Alcohols",

abstract = "A photochemical method for converting aliphatic alcohols into boronic esters is described. Preactivation of the alcohol as a 2‐iodophenyl‐thionocarbonate enables a novel Barton‐McCombie‐type radical deoxygenation that proceeds efficiently with visible light irradiation and without the requirement for a photocatalyst, a radical initiator, or tin or silicon hydrides. The resultant alkyl radical is intercepted by bis(catecholato)diboron, furnishing boronic esters from a diverse range of structurally complex alcohols.",

keywords = "Borons{\"a}ureester, Borylierungen, Desoxygenierung, Photochemie, Radikalreaktionen",

author = "Jingjing Wu and Robin Baer and Lin Guo and Adam Noble and Aggarwal, {Varinder Kumar}",

year = "2019",

month = oct,

day = "15",

doi = "10.1002/anie.201910051",

language = "English",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

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TY - JOUR

T1 - Photoinduced Deoxygenative Borylations of Aliphatic Alcohols

AU - Wu, Jingjing

AU - Baer, Robin

AU - Guo, Lin

AU - Noble, Adam

AU - Aggarwal, Varinder Kumar

PY - 2019/10/15

Y1 - 2019/10/15

N2 - A photochemical method for converting aliphatic alcohols into boronic esters is described. Preactivation of the alcohol as a 2‐iodophenyl‐thionocarbonate enables a novel Barton‐McCombie‐type radical deoxygenation that proceeds efficiently with visible light irradiation and without the requirement for a photocatalyst, a radical initiator, or tin or silicon hydrides. The resultant alkyl radical is intercepted by bis(catecholato)diboron, furnishing boronic esters from a diverse range of structurally complex alcohols.

AB - A photochemical method for converting aliphatic alcohols into boronic esters is described. Preactivation of the alcohol as a 2‐iodophenyl‐thionocarbonate enables a novel Barton‐McCombie‐type radical deoxygenation that proceeds efficiently with visible light irradiation and without the requirement for a photocatalyst, a radical initiator, or tin or silicon hydrides. The resultant alkyl radical is intercepted by bis(catecholato)diboron, furnishing boronic esters from a diverse range of structurally complex alcohols.

KW - Boronsäureester

KW - Borylierungen

KW - Desoxygenierung

KW - Photochemie

KW - Radikalreaktionen

U2 - 10.1002/anie.201910051

DO - 10.1002/anie.201910051

M3 - Article (Academic Journal)

C2 - 31613033

SN - 1433-7851

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

ER -

Photoinduced Deoxygenative Borylations of Aliphatic Alcohols

Abstract

Keywords

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Projects

FRESCO: Efficient, Flexible Synthesis of Molecules with Tailored Shapes: from Photoswitchable Helices to anti-Cancer Compounds

Cite this