Catalytic 2‑Ethylhexanoic Acid Promotes Mild Miyaura Borylations

The Miyaura borylation of aryl and heteroaryl chlorides and bromides using a combination of potassium carbonate and 5 mol % 2-ethylhexanoic acid at 25 °C is reported. The in situ generation of a catalytic amount of potassium 2-ethylhexanoate under these conditions avoids the need for special handlin...

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Published inJournal of organic chemistry Vol. 89; no. 8; pp. 5901 - 5904
Main Authors Klootwyk, Brittany M., Ruble, J. Craig, Cumming, Graham R., Woerly, Eric M.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.04.2024
Amer Chemical Soc
Subjects
carboxylic acids
Chemistry
Chemistry, Organic
heterocyclic compounds
organic chemistry
Physical Sciences
potassium
potassium carbonate
Science & Technology
stoichiometry
CROSS-COUPLING REACTION
HALOARENES
ARYL CHLORIDES
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Abstract The Miyaura borylation of aryl and heteroaryl chlorides and bromides using a combination of potassium carbonate and 5 mol % 2-ethylhexanoic acid at 25 °C is reported. The in situ generation of a catalytic amount of potassium 2-ethylhexanoate under these conditions avoids the need for special handling of stoichiometric quantities of hygroscopic potassium 2-ethylhexanoate during the reaction setup as well as difficulties in removing the resulting carboxylic acid during product isolation.
AbstractList The Miyaura borylation of aryl and heteroaryl chlorides and bromides using a combination of potassium carbonate and 5 mol % 2-ethylhexanoic acid at 25 °C is reported. The in situ generation of a catalytic amount of potassium 2-ethylhexanoate under these conditions avoids the need for special handling of stoichiometric quantities of hygroscopic potassium 2-ethylhexanoate during the reaction setup as well as difficulties in removing the resulting carboxylic acid during product isolation.The Miyaura borylation of aryl and heteroaryl chlorides and bromides using a combination of potassium carbonate and 5 mol % 2-ethylhexanoic acid at 25 °C is reported. The in situ generation of a catalytic amount of potassium 2-ethylhexanoate under these conditions avoids the need for special handling of stoichiometric quantities of hygroscopic potassium 2-ethylhexanoate during the reaction setup as well as difficulties in removing the resulting carboxylic acid during product isolation.
The Miyaura borylation of aryl and heteroaryl chlorides and bromides using a combination of potassium carbonate and 5 mol % 2-ethylhexanoic acid at 25(degrees)C is reported. The in situ generation of a catalytic amount of potassium 2-ethylhexanoate under these conditions avoids the need for special handling of stoichiometric quantities of hygroscopic potassium 2-ethylhexanoate during the reaction setup as well as difficulties in removing the resulting carboxylic acid during product isolation.
The Miyaura borylation of aryl and heteroaryl chlorides and bromides using a combination of potassium carbonate and 5 mol % 2-ethylhexanoic acid at 25 °C is reported. The in situ generation of a catalytic amount of potassium 2-ethylhexanoate under these conditions avoids the need for special handling of stoichiometric quantities of hygroscopic potassium 2-ethylhexanoate during the reaction setup as well as difficulties in removing the resulting carboxylic acid during product isolation.
The Miyaura borylation of aryl and heteroaryl chlorides and bromides using a combination of potassium carbonate and 5 mol % 2-ethylhexanoic acid at 25 °C is reported. The generation of a catalytic amount of potassium 2-ethylhexanoate under these conditions avoids the need for special handling of stoichiometric quantities of hygroscopic potassium 2-ethylhexanoate during the reaction setup as well as difficulties in removing the resulting carboxylic acid during product isolation.
Author Woerly, Eric M.
Cumming, Graham R.
Ruble, J. Craig
Klootwyk, Brittany M.
AuthorAffiliation Discovery Chemistry Research and Technologies, Lilly Research Laboratories
Eli Lilly and Company
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10.1021/acs.oprd.8b00312
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Snippet The Miyaura borylation of aryl and heteroaryl chlorides and bromides using a combination of potassium carbonate and 5 mol % 2-ethylhexanoic acid at 25 °C is...
The Miyaura borylation of aryl and heteroaryl chlorides and bromides using a combination of potassium carbonate and 5 mol % 2-ethylhexanoic acid at...
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SubjectTerms carboxylic acids
Chemistry
Chemistry, Organic
heterocyclic compounds
organic chemistry
Physical Sciences
potassium
potassium carbonate
Science & Technology
stoichiometry
Title Catalytic 2‑Ethylhexanoic Acid Promotes Mild Miyaura Borylations
URI http://dx.doi.org/10.1021/acs.joc.4c00280
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