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

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

7 Citations (Scopus)

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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1 Active

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

Aggarwal, V. K.

1/10/15 → 31/03/21

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Cite this

Wu, J., Baer, R., Guo, L., Noble, A., & Aggarwal, V. K. (2019). Photoinduced Deoxygenative Borylations of Aliphatic Alcohols. Angewandte Chemie - International Edition. https://doi.org/10.1002/anie.201910051

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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.",

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AU - Wu, Jingjing

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PY - 2019/10/15

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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

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DO - 10.1002/anie.201910051

M3 - Article (Academic Journal)

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JO - Angewandte Chemie - International Edition

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