Synthesis of Functionalized Dibenzothiophenes – An Efficient Three-Step Approach Based on Pd-Catalyzed C–C and C–S Bond Formations

Tue Heesgaard Jepsen; Mogens Larsen; Morten Jørgensen; Katarzyna A. Solanko; Andrew Bond; Anders Kadziola; Mogens Brøndsted Nielsen

Synthesis of Functionalized Dibenzothiophenes – An Efficient Three-Step Approach Based on Pd-Catalyzed C–C and C–S Bond Formations

Tue Heesgaard Jepsen, Mogens Larsen, Morten Jørgensen, Katarzyna A. Solanko, Andrew Bond, Anders Kadziola, Mogens Brøndsted Nielsen

Kemisk Institut

26 Citationer (Scopus)

Abstract

A novel and efficient three-step protocol for synthesizing functionalized dibenzothiophenes (DBTs) from common starting materials and by using palladium-catalyzed carbon-carbon and carbon-sulfur bond formations is presented. The reaction conditions offer significantly improved functional-group tolerance and regioselectivity as compared to previously reported methods. A flexible and concise three-step protocol for the synthesis of functionalized dibenzothiophenes DBTs from readily available starting materials is presented. The method is based on two palladium-catalyzed reactions to prepare the masked thiophenols 4followed by deprotection and in situ cyclization to form the DBT skeleton. This approach offers improved functional-group tolerance as well as regiocontrol in the synthesis of functionalized DBTs as compared to previously reported methods.

Originalsprog	Engelsk
Tidsskrift	European Journal of Organic Chemistry
Vol/bind	2011
Udgave nummer	1
Sider (fra-til)	53-57
ISSN	1434-193X
Status	Udgivet - jan. 2011

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http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201001393/abstract#!

Citationsformater

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title = "Synthesis of Functionalized Dibenzothiophenes – An Efficient Three-Step Approach Based on Pd-Catalyzed C–C and C–S Bond Formations",

abstract = "A novel and efficient three-step protocol for synthesizing functionalized dibenzothiophenes (DBTs) from common starting materials and by using palladium-catalyzed carbon-carbon and carbon-sulfur bond formations is presented. The reaction conditions offer significantly improved functional-group tolerance and regioselectivity as compared to previously reported methods. A flexible and concise three-step protocol for the synthesis of functionalized dibenzothiophenes DBTs from readily available starting materials is presented. The method is based on two palladium-catalyzed reactions to prepare the masked thiophenols 4followed by deprotection and in situ cyclization to form the DBT skeleton. This approach offers improved functional-group tolerance as well as regiocontrol in the synthesis of functionalized DBTs as compared to previously reported methods.",

author = "Jepsen, {Tue Heesgaard} and Mogens Larsen and Morten J{\o}rgensen and Solanko, {Katarzyna A.} and Andrew Bond and Anders Kadziola and Nielsen, {Mogens Br{\o}ndsted}",

year = "2011",

month = jan,

language = "English",

volume = "2011",

pages = "53--57",

journal = "European Journal of Organic Chemistry",

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T1 - Synthesis of Functionalized Dibenzothiophenes – An Efficient Three-Step Approach Based on Pd-Catalyzed C–C and C–S Bond Formations

AU - Jepsen, Tue Heesgaard

AU - Larsen, Mogens

AU - Jørgensen, Morten

AU - Solanko, Katarzyna A.

AU - Bond, Andrew

AU - Kadziola, Anders

AU - Nielsen, Mogens Brøndsted

PY - 2011/1

Y1 - 2011/1

N2 - A novel and efficient three-step protocol for synthesizing functionalized dibenzothiophenes (DBTs) from common starting materials and by using palladium-catalyzed carbon-carbon and carbon-sulfur bond formations is presented. The reaction conditions offer significantly improved functional-group tolerance and regioselectivity as compared to previously reported methods. A flexible and concise three-step protocol for the synthesis of functionalized dibenzothiophenes DBTs from readily available starting materials is presented. The method is based on two palladium-catalyzed reactions to prepare the masked thiophenols 4followed by deprotection and in situ cyclization to form the DBT skeleton. This approach offers improved functional-group tolerance as well as regiocontrol in the synthesis of functionalized DBTs as compared to previously reported methods.

AB - A novel and efficient three-step protocol for synthesizing functionalized dibenzothiophenes (DBTs) from common starting materials and by using palladium-catalyzed carbon-carbon and carbon-sulfur bond formations is presented. The reaction conditions offer significantly improved functional-group tolerance and regioselectivity as compared to previously reported methods. A flexible and concise three-step protocol for the synthesis of functionalized dibenzothiophenes DBTs from readily available starting materials is presented. The method is based on two palladium-catalyzed reactions to prepare the masked thiophenols 4followed by deprotection and in situ cyclization to form the DBT skeleton. This approach offers improved functional-group tolerance as well as regiocontrol in the synthesis of functionalized DBTs as compared to previously reported methods.

M3 - Journal article

SN - 1434-193X

VL - 2011

SP - 53

EP - 57

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 1

ER -

Synthesis of Functionalized Dibenzothiophenes – An Efficient Three-Step Approach Based on Pd-Catalyzed C–C and C–S Bond Formations

Abstract

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