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

Department of Chemistry

26 Citations (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.

Original language	English
Journal	European Journal of Organic Chemistry
Volume	2011
Issue number	1
Pages (from-to)	53-57
ISSN	1434-193X
Publication status	Published - Jan 2011

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Synthesis of Functionalized Dibenzothiophenes – An Efficient Three-Step Approach Based on Pd-Catalyzed C–C and C–S Bond Formations. / Jepsen, Tue Heesgaard; Larsen, Mogens; Jørgensen, Morten et al.

In: European Journal of Organic Chemistry, Vol. 2011, No. 1, 01.2011, p. 53-57.

Research output: Contribution to journal › Journal article › Research › peer-review

Jepsen, TH, Larsen, M, Jørgensen, M, Solanko, KA, Bond, A, Kadziola, A & Nielsen, MB 2011, 'Synthesis of Functionalized Dibenzothiophenes – An Efficient Three-Step Approach Based on Pd-Catalyzed C–C and C–S Bond Formations', European Journal of Organic Chemistry, vol. 2011, no. 1, pp. 53-57. <http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201001393/abstract#!>

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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.",

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AU - Jepsen, Tue Heesgaard

AU - Larsen, Mogens

AU - Jørgensen, Morten

AU - Solanko, Katarzyna A.

AU - Bond, Andrew

AU - Kadziola, Anders

AU - Nielsen, Mogens Brøndsted

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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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