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Catalytic C-H borylation using the five-coordinate tris-boryl complex (dippe)Ir(Bpin) 3 ( 5a , dippe = 1,2-bis(diisopropylphosphino)ethane) has been examined using 31 P{ 1 H} and 1 H NMR spectroscopy. Compound 5a was shown to react rapidly and reversibly with HBpin to generate a six-coordinate borylene complex, (dippe)Ir(H)-(Bpin) 2 (BOCMe 2 CMe 2 OBpin) ( 6 ), whose structure was confirmed by X-ray crystallography. Under catalytic conditions, the H 2 generated from C-H borylation converted compound 6 to a series of intermediates. The first is tentatively assigned from 31 P{ 1 H} and 1 H NMR spectra as (dippe)Ir(H 2 B 3 pin 3 ) ( 7 ), which is the product of formal H 2 addition to compound 5a . As catalysis progressed, compound 7 was converted to a new species with the formula (dippe)Ir(H 3 B 2 pin 2 ) ( 8 ), which arose from H 2 addition to compound 7 with loss of HBpin. Compound 8 was characterized by 31 P{ 1 H} and 1 H NMR spectroscopy, and its structure was confirmed by X-ray crystallography, where two molecules with different ligand orientations were found in the unit cell. DFT calculations support the formulation of compound 8 as an Ir III agostic borane complex, (dippe)IrH 2 (Bpin)(η 2 -HBpin). Compound 8 was gradually converted to (dippe)Ir(H 4 Bpin) ( 9 ), which was characterized by 31 P{ 1 H} and 1 H NMR spectroscopy and X-ray crystallography. DFT calculations favor its formulation as an agostic borane complex of Ir III with the formula (dippe)IrH 3 (η 2 -HBpin). Compound 9 reacted further with H 2 to afford the dimeric structure [(dippe)IrH 2 (μ 2 -H)] 2 ( 10 ), which was characterized by 1 H NMR and X-ray crystallography. Compounds 7-10 are in equilibrium when H 2 and HBpin are present.

organometallics

Reversible Borylene Formation from Ring Opening of Pinacolborane and Other Intermediates Generated from Five-Coordinate Tris-Boryl Complexes: Implications for Catalytic C–H Borylation