Base-Mediated Ring-Contraction of Pyran Systems Promoted by Palladium and Phase-Transfer Catalysis

Stuart Aiken, Orlando De Azevedo, Kieran Chauhan, Thomas Driscoll, Paul Elliott, Christopher Gabbutt, Mark Heron

Research output: Contribution to journalArticle

Abstract

A study of the ring-contraction of a model 3H-naphtho[2,1-b]pyran is described to elucidate and optimize the ring-contraction of naphthopyrans. Two efficient base-mediated protocols to access multiple naphthofurans, naphthodifurans, and a benzo-fused indole in generally good yields are reported. Furthermore, a protocol to selectively prepare (hetero)aryl-substituted naphthofurans via a Suzuki-coupling–ring-contraction process is presented. An additional protocol that allows Suzuki cross-coupling reactions to be performed on bromo-substituted naphthopyrans without the ring-contraction side reaction is reported.
Original languageEnglish
Number of pages15
JournalJournal of Organic Chemistry
Early online date20 Dec 2019
DOIs
Publication statusE-pub ahead of print - 20 Dec 2019

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Pyrans
Palladium
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title = "Base-Mediated Ring-Contraction of Pyran Systems Promoted by Palladium and Phase-Transfer Catalysis",
abstract = "A study of the ring-contraction of a model 3H-naphtho[2,1-b]pyran is described to elucidate and optimize the ring-contraction of naphthopyrans. Two efficient base-mediated protocols to access multiple naphthofurans, naphthodifurans, and a benzo-fused indole in generally good yields are reported. Furthermore, a protocol to selectively prepare (hetero)aryl-substituted naphthofurans via a Suzuki-coupling–ring-contraction process is presented. An additional protocol that allows Suzuki cross-coupling reactions to be performed on bromo-substituted naphthopyrans without the ring-contraction side reaction is reported.",
keywords = "ring-contraction, Pyran Systems, Palladium, Phase-Transfer Catalysis, Naphthofuran, Naphthodifuran, Benzindole",
author = "Stuart Aiken and {De Azevedo}, Orlando and Kieran Chauhan and Thomas Driscoll and Paul Elliott and Christopher Gabbutt and Mark Heron",
year = "2019",
month = "12",
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doi = "10.1021/acs.joc.9b02901",
language = "English",
journal = "Journal of Organic Chemistry",
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Base-Mediated Ring-Contraction of Pyran Systems Promoted by Palladium and Phase-Transfer Catalysis. / Aiken, Stuart; De Azevedo, Orlando; Chauhan, Kieran; Driscoll, Thomas; Elliott, Paul; Gabbutt, Christopher; Heron, Mark.

In: Journal of Organic Chemistry, 20.12.2019.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Base-Mediated Ring-Contraction of Pyran Systems Promoted by Palladium and Phase-Transfer Catalysis

AU - Aiken, Stuart

AU - De Azevedo, Orlando

AU - Chauhan, Kieran

AU - Driscoll, Thomas

AU - Elliott, Paul

AU - Gabbutt, Christopher

AU - Heron, Mark

PY - 2019/12/20

Y1 - 2019/12/20

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AB - A study of the ring-contraction of a model 3H-naphtho[2,1-b]pyran is described to elucidate and optimize the ring-contraction of naphthopyrans. Two efficient base-mediated protocols to access multiple naphthofurans, naphthodifurans, and a benzo-fused indole in generally good yields are reported. Furthermore, a protocol to selectively prepare (hetero)aryl-substituted naphthofurans via a Suzuki-coupling–ring-contraction process is presented. An additional protocol that allows Suzuki cross-coupling reactions to be performed on bromo-substituted naphthopyrans without the ring-contraction side reaction is reported.

KW - ring-contraction

KW - Pyran Systems

KW - Palladium

KW - Phase-Transfer Catalysis

KW - Naphthofuran

KW - Naphthodifuran

KW - Benzindole

U2 - 10.1021/acs.joc.9b02901

DO - 10.1021/acs.joc.9b02901

M3 - Article

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

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