Hydrogen atom transfer‐mediated cyclisations of nitriles

Oliver J. Turner; John A. Murphy; David J. Hirst; Eric P. A. Talbot

doi:10.1002/chem.201805236

Hydrogen atom transfer‐mediated cyclisations of nitriles

Oliver J. Turner
, John A. Murphy
, David J. Hirst
, Eric P. A. Talbot

Pure And Applied Chemistry

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

34 Citations (Scopus)

64 Downloads (Pure)

Abstract

Hydrogen atom transfer‐mediated intramolecular C−C coupling reactions between alkenes and nitriles, using PhSiH3 and catalytic Fe(acac)3, are described. This introduces a new strategic bond disconnection for ring‐closing reactions, forming ketones via imine intermediates. Of note is the scope of the reaction, including formation of sterically hindered ketones, spirocycles and fused cyclic systems.

Original language	English
Pages (from-to)	18658–18662
Number of pages	5
Journal	Chemistry - A European Journal
Volume	24
Issue number	70
Early online date	20 Oct 2018
DOIs	https://doi.org/10.1002/chem.201805236
Publication status	Published - 12 Dec 2018

Keywords

alkenes
nitriles
PhSiH3
catalytic Fe(acac)3
ring‐closing reactions
iron‐mediated HAT reactions

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Oliver-etal-Chemistry-2018-Hydrogen-atom-transfer-mediated-cyclisations-of-nitrilesAccepted author manuscript, 1.24 MB

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title = "Hydrogen atom transfer‐mediated cyclisations of nitriles",

abstract = "Hydrogen atom transfer‐mediated intramolecular C−C coupling reactions between alkenes and nitriles, using PhSiH3 and catalytic Fe(acac)3, are described. This introduces a new strategic bond disconnection for ring‐closing reactions, forming ketones via imine intermediates. Of note is the scope of the reaction, including formation of sterically hindered ketones, spirocycles and fused cyclic systems.",

keywords = "alkenes, nitriles, PhSiH3, catalytic Fe(acac)3, ring‐closing reactions, iron‐mediated HAT reactions",

author = "Turner, \{Oliver J.\} and Murphy, \{John A.\} and Hirst, \{David J.\} and Talbot, \{Eric P. A.\}",

note = "This is the peer reviewed version of the following article:Turner, O. J., Murphy, J. A., Hirst, D. J., \& Talbot, E. P. A. (2018). Hydrogen atom transfer‐mediated cyclisations of nitriles. Chemistry - A European Journal, 24(70), 18658–18662., which has been published in final form at https://doi.org/10.1002/chem.201805236. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.",

year = "2018",

month = dec,

day = "12",

doi = "10.1002/chem.201805236",

language = "English",

volume = "24",

pages = "18658–18662",

journal = "Chemistry - A European Journal",

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publisher = "John Wiley and Sons Inc.",

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TY - JOUR

T1 - Hydrogen atom transfer‐mediated cyclisations of nitriles

AU - Turner, Oliver J.

AU - Murphy, John A.

AU - Hirst, David J.

AU - Talbot, Eric P. A.

N1 - This is the peer reviewed version of the following article:Turner, O. J., Murphy, J. A., Hirst, D. J., & Talbot, E. P. A. (2018). Hydrogen atom transfer‐mediated cyclisations of nitriles. Chemistry - A European Journal, 24(70), 18658–18662., which has been published in final form at https://doi.org/10.1002/chem.201805236. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.

PY - 2018/12/12

Y1 - 2018/12/12

N2 - Hydrogen atom transfer‐mediated intramolecular C−C coupling reactions between alkenes and nitriles, using PhSiH3 and catalytic Fe(acac)3, are described. This introduces a new strategic bond disconnection for ring‐closing reactions, forming ketones via imine intermediates. Of note is the scope of the reaction, including formation of sterically hindered ketones, spirocycles and fused cyclic systems.

AB - Hydrogen atom transfer‐mediated intramolecular C−C coupling reactions between alkenes and nitriles, using PhSiH3 and catalytic Fe(acac)3, are described. This introduces a new strategic bond disconnection for ring‐closing reactions, forming ketones via imine intermediates. Of note is the scope of the reaction, including formation of sterically hindered ketones, spirocycles and fused cyclic systems.

KW - alkenes

KW - nitriles

KW - PhSiH3

KW - catalytic Fe(acac)3

KW - ring‐closing reactions

KW - iron‐mediated HAT reactions

U2 - 10.1002/chem.201805236

DO - 10.1002/chem.201805236

M3 - Article

SN - 0947-6539

VL - 24

SP - 18658

EP - 18662

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 70

ER -

Hydrogen atom transfer‐mediated cyclisations of nitriles

Abstract

Keywords

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