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Experimental and Computational Evidence for a Boron-Assisted, σ-Bond Metathesis Pathway for Alkane Borylation

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Department of Chemistry, Texas A&M University, College Station, Texas 77843-3255, and Department of Chemistry, 225 Prospect Street, P.O. Box 208107, Yale University, New Haven, Connecticut 06520-8107
Cite this: J. Am. Chem. Soc. 2003, 125, 4, 858–859
Publication Date (Web):January 3, 2003
https://doi.org/10.1021/ja028394c
Copyright © 2003 American Chemical Society
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Photoejection of one CO ligand from isolated CpM(CO)n+1BR2 (n = 1:  M = Fe, Ru; n = 2:  M = Mo,W; R2 = catecholate or pinacolate) compounds produces a coordinatively unsaturated 16 e- intermediate, a cyclic dioxaboryl transition metal complex, that can efficiently and selectively initiate regioselective C−H bond activation and can be used in the functionalization of alkanes. This chemistry appears distinct from that reported previously for related CpM(CO)n complexes of alkyl and aryl ligands. We show here by a combination of experimental and theoretical studies that the “unoccupied” p orbital of dioxaboryl ligands are intimately involved in the C−H bond activation step and that this hydrogen transfer to boron occurs by a boron-assisted, metal-mediated σ-bond metathesis. The “unoccupied” p orbital of boron lowers the energy of the transition state and the intermediates by accepting electron density from the metal. The metal-bound borane then rotates, transfers back through a σ-bond metathesis to capture the alkyl, and leaves the metal hydride.

†

 Texas A&M University.

*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

‡

 Yale University.

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Synthesis, photochemistry, and spectral data for 1−3 and 6−8, structures of 9−15, percentage atomic character in Boys localized orbitals, and details of the Mulliken population analysis (PDF). This material is available free of charge via the Internet at http://pubs.acs.org.

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