A Mitsunobu reaction to functionalized cyclic and bicyclic N-arylamines

Daniel Gill; Matthew Iveson; Ian Collins; Alan M. Jones

doi:10.1016/j.tetlet.2017.12.017

A Mitsunobu reaction to functionalized cyclic and bicyclic N-arylamines

Daniel Gill, Matthew Iveson, Ian Collins, Alan M. Jones

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Abstract

The scope of an unexpected Mitsunobu cyclisation to prepare N-arylated Fsp3-enriched azacycles was investigated. In the current study, we have identified whether a pKa-dependent Mitsunobu cyclodehydration or a pKa-independent Mitsunobu intramolecular reaction was in operation. A Mitsunobu reaction, creating a leaving group, followed by intramolecular nucleophilic displacement was determined to be the dominant pathway.

Original language	English
Journal	Tetrahedron Letters
Volume	59
Issue number	3
Early online date	6 Dec 2017
DOIs	https://doi.org/10.1016/j.tetlet.2017.12.017
Publication status	Published - 17 Jan 2018

Keywords

mitsunobu
cyclodehydration
nucleophilic aromatic substitution
intramolecular
cyclisation

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10.1016/j.tetlet.2017.12.017

Gill_et_al_A_Mitsunobu_reaction_to_Tetrahedron_Letters_2017
Checked for eligibility: 16/01/2018
Accepted author manuscript, 138 KBLicence: Creative Commons: Attribution-NonCommercial-NoDerivs (CC BY-NC-ND)

https://www.sciencedirect.com/science/article/pii/S0040403917315095Licence: None: All rights reserved

Cite this

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title = "A Mitsunobu reaction to functionalized cyclic and bicyclic N-arylamines",

abstract = "The scope of an unexpected Mitsunobu cyclisation to prepare N-arylated Fsp3-enriched azacycles was investigated. In the current study, we have identified whether a pKa-dependent Mitsunobu cyclodehydration or a pKa-independent Mitsunobu intramolecular reaction was in operation. A Mitsunobu reaction, creating a leaving group, followed by intramolecular nucleophilic displacement was determined to be the dominant pathway.",

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T1 - A Mitsunobu reaction to functionalized cyclic and bicyclic N-arylamines

AU - Gill, Daniel

AU - Iveson, Matthew

AU - Collins, Ian

AU - Jones, Alan M.

PY - 2018/1/17

Y1 - 2018/1/17

N2 - The scope of an unexpected Mitsunobu cyclisation to prepare N-arylated Fsp3-enriched azacycles was investigated. In the current study, we have identified whether a pKa-dependent Mitsunobu cyclodehydration or a pKa-independent Mitsunobu intramolecular reaction was in operation. A Mitsunobu reaction, creating a leaving group, followed by intramolecular nucleophilic displacement was determined to be the dominant pathway.

AB - The scope of an unexpected Mitsunobu cyclisation to prepare N-arylated Fsp3-enriched azacycles was investigated. In the current study, we have identified whether a pKa-dependent Mitsunobu cyclodehydration or a pKa-independent Mitsunobu intramolecular reaction was in operation. A Mitsunobu reaction, creating a leaving group, followed by intramolecular nucleophilic displacement was determined to be the dominant pathway.

KW - mitsunobu

KW - cyclodehydration

KW - nucleophilic aromatic substitution

KW - intramolecular

KW - cyclisation

U2 - 10.1016/j.tetlet.2017.12.017

DO - 10.1016/j.tetlet.2017.12.017

M3 - Article

SN - 0040-4039

VL - 59

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 3

ER -

A Mitsunobu reaction to functionalized cyclic and bicyclic N-arylamines

Abstract

Keywords

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