Fusing Carborane Carboxylic Acids with Alkynes: 3D Analogues of Isocoumarins via Regioselective B−H Activation

An iridium‐catalyzed alkenylation/annulation sequence between monocarba‐closo‐dodecaborate carboxylic acids and diarylacetylenes is reported. Regioselective activation of the B2 position, followed by B−C bond formation and ring closure, affords 3D bora‐analogues of isocoumarins. The reaction tolerat...

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Bibliographic Details
Published in:Chemistry : a European journal 2018-01, Vol.24 (3), p.551-555
Main Authors: Lin, Furong, Shen, Yunjun, Zhang, Yuanbin, Sun, Yuji, Liu, Jiyong, Duttwyler, Simon
Format: Article
Language:English
Subjects:
Activation
Alkynes
annulation
Aromatic compounds
B−H activation
Carborane
Carboxylic acids
Chemical reactions
Chemistry
Functional groups
Iridium
iridium catalysis
isocoumarin
Organic chemistry
Regioselectivity
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Summary:An iridium‐catalyzed alkenylation/annulation sequence between monocarba‐closo‐dodecaborate carboxylic acids and diarylacetylenes is reported. Regioselective activation of the B2 position, followed by B−C bond formation and ring closure, affords 3D bora‐analogues of isocoumarins. The reaction tolerates a variety of functional groups on the aromatic rings and can be extended to B12‐substituted derivatives. Furthermore, subsequent alkenylation of the B4 vertex has been achieved in high yields. Get 3D! An iridium‐catalyzed alkenylation/annulation sequence between carborane carboxylic acids and alkynes is reported. Regioselective activation of the B2 position, followed by B−C bond formation and ring closure, affords 3D bora‐analogues of isocoumarins.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201703802