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Fusing Carborane Carboxylic Acids with Alkynes: 3D Analogues of Isocoumarins via Regioselective B−H Activation
Author(s) -
Lin Furong,
Shen Yunjun,
Zhang Yuanbin,
Sun Yuji,
Liu Jiyong,
Duttwyler Simon
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201703802
Subject(s) - regioselectivity , isocoumarins , chemistry , annulation , ring (chemistry) , stereochemistry , combinatorial chemistry , medicinal chemistry , catalysis , organic chemistry
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.