Catalytic Conjunctive Coupling of Carboxylic Acid Derivatives with 9‐BBN‐Derived Ate Complexes

β‐Boryl carbonyl compounds are produced by a Ni‐catalyzed cross‐coupling of vinylboron “ate” complexes and acid chloride or acid anhydride electrophiles. The reactions are efficient, being complete in as little as two minutes, and can be applied to a broad range of substrates. Conjunctive Coupling:...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-05, Vol.58 (20), p.6654-6658
Main Authors: Law, Chunyin, Meng, Yan, Koo, Seung Moh, Morken, James P.
Format: Article
Language:English
Subjects:
Acidic oxides
Anhydrides
boron
Boron - metabolism
Carbonyl compounds
Carbonyls
Carboxylic acids
Carboxylic Acids - metabolism
Catalysis
conjugative coupling
Coupling (molecular)
cross-coupling
Humans
nickel
Organic Chemicals
Substrates
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Summary:β‐Boryl carbonyl compounds are produced by a Ni‐catalyzed cross‐coupling of vinylboron “ate” complexes and acid chloride or acid anhydride electrophiles. The reactions are efficient, being complete in as little as two minutes, and can be applied to a broad range of substrates. Conjunctive Coupling: A new route to synthetically useful β‐boryl carbonyls is enabled by the Ni‐catalyzed addition of alkenyl boron ate complexes to activated carboxylic acids. The reactions are efficient, being complete in as little as two minutes, and can be applied to a broad range of substrates.
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201901927