期刊
ACS CATALYSIS
卷 11, 期 21, 页码 13445-13451出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c03888
关键词
C-H activation; organoboron; P-chiral phosphorus; synthetic methods; asymmetric catalysis
资金
- National Natural Science Foundation of China [91956116, 21973113]
- Guangdong Natural Science Funds for Distinguished Young Scholar [2015A030306027]
- Lanzhou Institute of Chemical Physics
- Hangzhou Normal University
This study presents a novel method for the synthesis of P-stereogenic phosphorus compounds through phosphinate-directed iridium-catalyzed reactions, with high yields and good enantioselectivities. The borylated products synthesized can be used for the preparation of precursors for chiral phosphine ligands, showing potential industrial applications.
P-stereogenic phosphorus compounds are a ubiquitous and critically important class of chiral ligands in asymmetric catalysis. Methods for catalytic asymmetric synthesis via a step- and atom-economic way are still very limited. We herein disclose a protocol of phosphinate-directed iridium-catalyzed enantioselective ortho-H borylation to construct P-stereogenic phosphorus compounds. A number of functional groups could be well tolerated to afford optically active diarylphosphinates with good to excellent enantioselectivities (up to 92% ee). We also demonstrate the synthetic utilities of the obtained borylated products, including the synthesis of precursors for chiral phosphine ligands.
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