Fusing Carborane Carboxylic Acids with Alkynes: 3D Analogues of Isocoumarins via Regioselective B−H Activation. Issue 3 (25th October 2017)

• Record Type: Journal Article
• Authors: Lin, Furong; Shen, Yunjun; Zhang, Yuanbin; Sun, Yuji; Liu, Jiyong; Duttwyler, Simon
• Is Part Of: Chemistry. Volume 24:Issue 3(2018)
• Page Start: 551
• Page End: 555
• Publication Date: 2017-10-25
• Subjects: annulation -- B−H activation -- carborane -- iridium catalysis -- isocoumarin; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201703802
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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. Abstract : 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.