期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 139, 期 23, 页码 7729-7732出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b04080
关键词
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资金
- American Chemical Society Petroleum Research Fund [56562-DNI3]
- UCLA
- 3M (Non-Tenured Faculty Award)
- National Defense Science and Engineering Graduate Fellowship Program
- NSF [CHE-1048804, CHE1361104]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1361104] Funding Source: National Science Foundation
We report the first observed Pd-catalyzed isomerization (cage-walking) of B(9)-bromo-meta-carborane during Pd-catalyzed cross-coupling, which enables the formation of B-O and B-N bonds at all boron vertices (B(2), B(4), B(5), and B(9)) of meta-carborane. Experimental and theoretical studies suggest this isomerization mechanism is strongly influenced by the steric crowding at the Pd catalyst by either a biaryl phosphine ligand and/or substrate. Ultimately, this cage-walking process provides a unique pathway to preferentially introduce functional groups at the B(2) vertex using B(9)-bromo-meta-carborane as the sole starting material through substrate control.
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