Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 24, Pages 9504-9510Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b03862
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Funding
- National Key R&D Program of China [2016YFA0202900]
- National Natural Science Foundation of China [21821002, 91856201, 21572250]
- CAS [XDB20000000, QYZDY-SSW-SLH012]
- Science and Technology Commission of Shanghai Municipality [18JC1411302]
- China Postdoctoral Science Foundation [2019M650092]
- Pharmaron
- Initiative Postdocs Supporting Program [BX20180342]
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Rhodium(I)-catalyzed atroposelective C-H arylation of heterobiaryls was presented. In the presence of a Rh catalyst derived from [Rh(C2H4)(2) CH2 and a TADDOL-derived monodentate phosphonite, with 2-pyridine, 2-isoquinoline and their analogs as directing groups, a series of axially chiral heterobiaryls were obtained in excellent yields and enantioselectivities (up to 99% yield, 97% ee) via C-H direct functionalization reaction. The products obtained from this method provide a platform for the synthesis of axially chiral biaryl ligands and catalysts. As a demonstration, a chiral N-oxide synthesized from the product in one step could act as an efficient catalyst for asymmetric allylation of benzaldehyde with allyltrichlorosilane, leading to homoallyl alcohol with excellent enantiocontrol.
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