Regioselective synthesis of 1- and 4-tetralones from heteroaryl-3-cyclobutanols

Philipp Natho; Annie B. Rouse; Jake L. Greenfield; Lewis A.T. Allen; Andrew J.P. White; Zeyu Yang; Philip J. Parsons

doi:10.1016/j.tet.2020.131636

Regioselective synthesis of 1- and 4-tetralones from heteroaryl-3-cyclobutanols

Philipp Natho, Annie B. Rouse, Jake L. Greenfield, Lewis A.T. Allen, Andrew J.P. White, Zeyu Yang, Philip J. Parsons^*

^*Corresponding author for this work

School of Chemistry

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

Abstract

Herein we describe the first transition-metal-free ring expansion of four-membered rings to 1-tetralones from 3-substituted heteroaromatic compounds, and the first example of an oxetanol ring expansion to an oxa-tetralone. We also experimentally investigate the mechanism of the silver-mediated ring expansion and elucidate the active oxidant in these systems using electrochemical techniques.

Original language	English
Article number	131636
Journal	Tetrahedron
Volume	76
Issue number	47
DOIs	https://doi.org/10.1016/j.tet.2020.131636
Publication status	Published - 20 Nov 2020

Keywords

Cyclic voltammetry
Cyclobutanols
Divergent synthesis
Heteroaromatics
Ring expansion

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10.1016/j.tet.2020.131636

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title = "Regioselective synthesis of 1- and 4-tetralones from heteroaryl-3-cyclobutanols",

abstract = "Herein we describe the first transition-metal-free ring expansion of four-membered rings to 1-tetralones from 3-substituted heteroaromatic compounds, and the first example of an oxetanol ring expansion to an oxa-tetralone. We also experimentally investigate the mechanism of the silver-mediated ring expansion and elucidate the active oxidant in these systems using electrochemical techniques.",

keywords = "Cyclic voltammetry, Cyclobutanols, Divergent synthesis, Heteroaromatics, Ring expansion",

author = "Philipp Natho and Rouse, \{Annie B.\} and Greenfield, \{Jake L.\} and Allen, \{Lewis A.T.\} and White, \{Andrew J.P.\} and Zeyu Yang and Parsons, \{Philip J.\}",

note = "Publisher Copyright: {\textcopyright} 2020 Elsevier Ltd",

year = "2020",

month = nov,

day = "20",

doi = "10.1016/j.tet.2020.131636",

language = "English",

volume = "76",

journal = "Tetrahedron",

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TY - JOUR

T1 - Regioselective synthesis of 1- and 4-tetralones from heteroaryl-3-cyclobutanols

AU - Natho, Philipp

AU - Rouse, Annie B.

AU - Greenfield, Jake L.

AU - Allen, Lewis A.T.

AU - White, Andrew J.P.

AU - Yang, Zeyu

AU - Parsons, Philip J.

PY - 2020/11/20

Y1 - 2020/11/20

N2 - Herein we describe the first transition-metal-free ring expansion of four-membered rings to 1-tetralones from 3-substituted heteroaromatic compounds, and the first example of an oxetanol ring expansion to an oxa-tetralone. We also experimentally investigate the mechanism of the silver-mediated ring expansion and elucidate the active oxidant in these systems using electrochemical techniques.

AB - Herein we describe the first transition-metal-free ring expansion of four-membered rings to 1-tetralones from 3-substituted heteroaromatic compounds, and the first example of an oxetanol ring expansion to an oxa-tetralone. We also experimentally investigate the mechanism of the silver-mediated ring expansion and elucidate the active oxidant in these systems using electrochemical techniques.

KW - Cyclic voltammetry

KW - Cyclobutanols

KW - Divergent synthesis

KW - Heteroaromatics

KW - Ring expansion

UR - https://www.scopus.com/pages/publications/85092491400

U2 - 10.1016/j.tet.2020.131636

DO - 10.1016/j.tet.2020.131636

M3 - Article

AN - SCOPUS:85092491400

SN - 0040-4020

VL - 76

JO - Tetrahedron

JF - Tetrahedron

IS - 47

M1 - 131636

ER -

Regioselective synthesis of 1- and 4-tetralones from heteroaryl-3-cyclobutanols

Abstract

Keywords

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