Borylation of fluorinated arenes using the boron-centred nucleophile B(CN)32- - a unique entry to aryltricyanoborates.

Borylation of fluorinated arenes using the boron-centred nucleophile B(CN)3 2– – a unique entry to aryltricyanoborates† †Electronic supplementary information (ESI) available: Additional tables, experimental information, analytical data and details of the DFT calculations. CCDC 1548893–1548910. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc02249b Click here for additional data file. Click here for additional data file.

Iridium/N-heterocyclic carbene-catalyzed C–H borylation of arenes by diisopropylaminoborane

Catalytic C-H borylation of arenes has been widely used in organic synthesis because it allows the introduction of a versatile boron functionality directly onto simple, unfunctionalized arenes. We report herein the use of diisopropylaminoborane as a boron source in C-H borylation of arenes. An iridium(I) complex with 1,3-dicyclohexylimidazol-2-ylidene is found to efficiently catalyze the boryla...

Convenient access to the tricyanoborate dianion B(CN)₃²⁻ and selected reactions as a boron-centred nucleophile.

Alkali metal tricyanoborates M2B(CN)3 (M = Na, K) are accessible by the reaction of tricyanofluoroborates with alkali metals (i) in liquid NH3 or (ii) in THF-naphthalene. The M2B(CN)3 are versatile starting materials for the synthesis of K[RB(CN)3] (R = Et, C6F5, CH2=CHCH2).

Iridium-bipyridine periodic mesoporous organosilica catalyzed direct C-H borylation using a pinacolborane.

Heterogeneous catalysis for direct C-H borylation of arenes and heteroarenes in the combination of iridium (Ir) complex fixed on periodic mesoporous organosilica containing bipyridine ligands within the framework (Ir-BPy-PMO) and pinacolborane (HBpin) is reported. Ir-BPy-PMO showed higher catalytic activity toward the borylation of benzene with inexpensive HBpin compared to expensive bis(pinaco...

Efficient Rh-catalyzed C-H borylation of arene derivatives under photochemical conditions.

Photocatalysis allows innovations in organic synthesis. Among the various catalytic reactions, CH-functionalizations offer valuable possibilities for the refinement of easily available building blocks. In this respect, catalytic borylation is of interest, too. So far, most of the catalytic borylation reactions are performed under thermal conditions at comparably high temperatures. Here, we desc...