The McKenna reaction – avoiding side reactions in phosphonate deprotection

The McKenna reaction is a well-known and popular method for the efficient and mild synthesis of organophosphorus acids. Bromotrimethylsilane (BTMS) is the main reagent in this reaction, which transforms dialkyl phosphonate esters into bis(trimethylsilyl)esters, which are then easily converted into t...

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Main Authors:	Katarzyna Justyna, Joanna Małolepsza, Damian Kusy, Waldemar Maniukiewicz, Katarzyna M. Błażewska
Format:	Article
Language:	English
Published:	Beilstein-Institut 2020-06-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	bromotrimethylsilane mckenna reaction organophosphorus acid oxazole phosphonate ester
Online Access:	https://doi.org/10.3762/bjoc.16.119

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spelling	doaj-fae351d4fa274e52b0513133490cb8832021-04-02T12:42:06ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-06-011611436144610.3762/bjoc.16.1191860-5397-16-119The McKenna reaction – avoiding side reactions in phosphonate deprotectionKatarzyna Justyna0Joanna Małolepsza1Damian Kusy2Waldemar Maniukiewicz3Katarzyna M. Błażewska4Institute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, Zeromskiego St. 116, 90-924 Lodz, PolandInstitute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, Zeromskiego St. 116, 90-924 Lodz, PolandInstitute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, Zeromskiego St. 116, 90-924 Lodz, PolandInstitute of General and Ecological Chemistry, Faculty of Chemistry, Lodz University of Technology, Zeromskiego St. 116, 90-924 Lodz, PolandInstitute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, Zeromskiego St. 116, 90-924 Lodz, PolandThe McKenna reaction is a well-known and popular method for the efficient and mild synthesis of organophosphorus acids. Bromotrimethylsilane (BTMS) is the main reagent in this reaction, which transforms dialkyl phosphonate esters into bis(trimethylsilyl)esters, which are then easily converted into the target acids. However, the versatile character of the McKenna reaction is not always used to its full extent, due to formation of side products. Herein, demonstrated by using model examples we have not only analyzed the typical side processes accompanying the McKenna reaction, but also uncovered new ones. Further, we discovered that some commonly recommended precautions did not always circumvent the side reactions. The proposed results and recommendations may facilitate the synthesis of phosphonic acids.https://doi.org/10.3762/bjoc.16.119bromotrimethylsilanemckenna reactionorganophosphorus acidoxazolephosphonate ester
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Katarzyna Justyna Joanna Małolepsza Damian Kusy Waldemar Maniukiewicz Katarzyna M. Błażewska
spellingShingle	Katarzyna Justyna Joanna Małolepsza Damian Kusy Waldemar Maniukiewicz Katarzyna M. Błażewska The McKenna reaction – avoiding side reactions in phosphonate deprotection Beilstein Journal of Organic Chemistry bromotrimethylsilane mckenna reaction organophosphorus acid oxazole phosphonate ester
author_facet	Katarzyna Justyna Joanna Małolepsza Damian Kusy Waldemar Maniukiewicz Katarzyna M. Błażewska
author_sort	Katarzyna Justyna
title	The McKenna reaction – avoiding side reactions in phosphonate deprotection
title_short	The McKenna reaction – avoiding side reactions in phosphonate deprotection
title_full	The McKenna reaction – avoiding side reactions in phosphonate deprotection
title_fullStr	The McKenna reaction – avoiding side reactions in phosphonate deprotection
title_full_unstemmed	The McKenna reaction – avoiding side reactions in phosphonate deprotection
title_sort	mckenna reaction – avoiding side reactions in phosphonate deprotection
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2020-06-01
description	The McKenna reaction is a well-known and popular method for the efficient and mild synthesis of organophosphorus acids. Bromotrimethylsilane (BTMS) is the main reagent in this reaction, which transforms dialkyl phosphonate esters into bis(trimethylsilyl)esters, which are then easily converted into the target acids. However, the versatile character of the McKenna reaction is not always used to its full extent, due to formation of side products. Herein, demonstrated by using model examples we have not only analyzed the typical side processes accompanying the McKenna reaction, but also uncovered new ones. Further, we discovered that some commonly recommended precautions did not always circumvent the side reactions. The proposed results and recommendations may facilitate the synthesis of phosphonic acids.
topic	bromotrimethylsilane mckenna reaction organophosphorus acid oxazole phosphonate ester
url	https://doi.org/10.3762/bjoc.16.119
work_keys_str_mv	AT katarzynajustyna themckennareactionavoidingsidereactionsinphosphonatedeprotection AT joannamałolepsza themckennareactionavoidingsidereactionsinphosphonatedeprotection AT damiankusy themckennareactionavoidingsidereactionsinphosphonatedeprotection AT waldemarmaniukiewicz themckennareactionavoidingsidereactionsinphosphonatedeprotection AT katarzynambłazewska themckennareactionavoidingsidereactionsinphosphonatedeprotection AT katarzynajustyna mckennareactionavoidingsidereactionsinphosphonatedeprotection AT joannamałolepsza mckennareactionavoidingsidereactionsinphosphonatedeprotection AT damiankusy mckennareactionavoidingsidereactionsinphosphonatedeprotection AT waldemarmaniukiewicz mckennareactionavoidingsidereactionsinphosphonatedeprotection AT katarzynambłazewska mckennareactionavoidingsidereactionsinphosphonatedeprotection
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The McKenna reaction – avoiding side reactions in phosphonate deprotection

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