Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 9, Pages 2834-2838Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201812857
Keywords
ambiphilic molecules; borylation; C-H functionalization; homogeneous catalysis; phosphorus
Categories
Funding
- American Chemical Society Petroleum Research Fund [54825-UR3]
- Henry Dreyfus Foundation
- National Science Foundation [CHE-1764307, 0417731, CHE-1126585]
- Doheny Foundation
- Farrell Family
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0417731] Funding Source: National Science Foundation
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Ambiphilic molecules, which contain a Lewis base and Lewis acid, are of great interest based on their unique ability to activate small molecules. Phosphine boronates are one class of these substrates that have interesting catalytic activity. Direct access to these phosphine boronates is described through the iridium-catalyzed C-H borylation of phosphines. An unconventional cationic iridium catalyst was identified as optimal for a range of phosphines, providing good yields and selectivity across a diverse class of phosphine boronates (isolated as the borane-protected phosphine). A complimentary catalyst system (quinoline-based silane ligand with [(COD)IrOMe](2)) was optimal for biphenyl-based phosphines. Selective polyborylation was also shown providing bis- and tris-borylated phosphines. Deprotection of the phosphine boronate provided free ambiphilic phosphine boronates, which do not have detectable interactions between the phosphorus and boron atoms in solution or the solid state.
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