Deaminative Borylation of Aliphatic Amines Enabled by Visible Light Excitation of an Electron Donor–Acceptor Complex

Frederik Sandfort; Felix Strieth-Kalthoff; Felix J.R. Klauck; Michael J. James; Frank Glorius

doi:10.1002/chem.201804246

Deaminative Borylation of Aliphatic Amines Enabled by Visible Light Excitation of an Electron Donor–Acceptor Complex

Frederik Sandfort, Felix Strieth-Kalthoff, Felix J.R. Klauck, Michael J. James, Frank Glorius^*

^*Corresponding author for this work

Chemistry

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

Abstract

A deaminative strategy for the borylation of aliphatic primary amines is described. Alkyl radicals derived from the single-electron reduction of redox-active pyridinium salts, which can be isolated or generated in situ, were borylated in a visible light-mediated reaction with bis(catecholato)diboron. No catalyst or further additives were required. The key electron donor–acceptor complex was characterized in detail by both experimental and computational investigations. The synthetic potential of this mild protocol was demonstrated through the late-stage functionalization of natural products and drug molecules.

Original language	English
Pages (from-to)	17210-17214
Number of pages	5
Journal	Chemistry - A European Journal
Volume	24
Issue number	65
Early online date	30 Oct 2018
DOIs	https://doi.org/10.1002/chem.201804246
Publication status	Published - 23 Nov 2018

Keywords

borylation
deaminative strategy
DFT calculations
electron donor–acceptor
visible light

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10.1002/chem.201804246

Deaminative BorylationAccepted author manuscript, 1.24 MB

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title = "Deaminative Borylation of Aliphatic Amines Enabled by Visible Light Excitation of an Electron Donor–Acceptor Complex",

abstract = "A deaminative strategy for the borylation of aliphatic primary amines is described. Alkyl radicals derived from the single-electron reduction of redox-active pyridinium salts, which can be isolated or generated in situ, were borylated in a visible light-mediated reaction with bis(catecholato)diboron. No catalyst or further additives were required. The key electron donor–acceptor complex was characterized in detail by both experimental and computational investigations. The synthetic potential of this mild protocol was demonstrated through the late-stage functionalization of natural products and drug molecules.",

keywords = "borylation, deaminative strategy, DFT calculations, electron donor–acceptor, visible light",

author = "Frederik Sandfort and Felix Strieth-Kalthoff and Klauck, {Felix J.R.} and James, {Michael J.} and Frank Glorius",

year = "2018",

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T1 - Deaminative Borylation of Aliphatic Amines Enabled by Visible Light Excitation of an Electron Donor–Acceptor Complex

AU - Sandfort, Frederik

AU - Strieth-Kalthoff, Felix

AU - Klauck, Felix J.R.

AU - James, Michael J.

AU - Glorius, Frank

PY - 2018/11/23

Y1 - 2018/11/23

N2 - A deaminative strategy for the borylation of aliphatic primary amines is described. Alkyl radicals derived from the single-electron reduction of redox-active pyridinium salts, which can be isolated or generated in situ, were borylated in a visible light-mediated reaction with bis(catecholato)diboron. No catalyst or further additives were required. The key electron donor–acceptor complex was characterized in detail by both experimental and computational investigations. The synthetic potential of this mild protocol was demonstrated through the late-stage functionalization of natural products and drug molecules.

AB - A deaminative strategy for the borylation of aliphatic primary amines is described. Alkyl radicals derived from the single-electron reduction of redox-active pyridinium salts, which can be isolated or generated in situ, were borylated in a visible light-mediated reaction with bis(catecholato)diboron. No catalyst or further additives were required. The key electron donor–acceptor complex was characterized in detail by both experimental and computational investigations. The synthetic potential of this mild protocol was demonstrated through the late-stage functionalization of natural products and drug molecules.

KW - borylation

KW - deaminative strategy

KW - DFT calculations

KW - electron donor–acceptor

KW - visible light

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JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 65

ER -

Deaminative Borylation of Aliphatic Amines Enabled by Visible Light Excitation of an Electron Donor–Acceptor Complex

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Michael John James

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Deaminative Borylation of Aliphatic Amines Enabled by Visible Light Excitation of an Electron Donor–Acceptor Complex

Abstract

Keywords

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Michael John James

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