Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 28, Issue 51, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202202074
Keywords
borylation; iridium catalysis; late-stage functionalization; ligand libraries; phosphines
Categories
Funding
- Lise-Meitner Program of the MPG
- China Scholarship Council (CSC)
Ask authors/readers for more resources
This article introduces a novel method for fine-tuning phosphine ligands, which enables diversification of phosphine compounds by introducing different substituents into previously inaccessible positions. Compared to existing methods, this approach overcomes the limitations of phosphorus-directed reactions.
The fine-tuning of metal-phosphine-catalyzed reactions relies largely on accessing ever more precisely tuned phosphine ligands by de-novo synthesis. Late-stage C-H functionalization and diversification of commercial phosphines offers rapid access to entire libraries of derivatives based on privileged scaffolds. But existing routes, relying on phosphorus-directed transformations, only yield functionalization of Csp2 -H bonds in a specific position relative to phosphorus. In contrast to phosphorus-directed strategies, herein we disclose an orthogonal functionalization strategy capable of introducing a range of substituents into previously inaccessible positions on arylphosphines. The strongly coordinating phosphine group acts solely as a bystander in the sterically controlled borylation of bulky phosphines, and the resulting borylated phosphines serve as the supporting ligands for palladium during diversification through phosphine self-assisted Suzuki-Miyaura reactions.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available