Enantioselective synthesis of chiral heterocyclic biaryls via asymmetric Suzuki–Miyaura cross-coupling of 3-bromopyridine derivatives
A series of chiral heterocyclic biaryls with a pyridyl moiety were prepared in moderate to good yields with up to 92% ee via asymmetric Suzuki–Miyaura coupling. The chiral-bridged biphenyl monophosphine ligand L1 was found to be much more effective in the reaction enantioselection than its counterpa...
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| Published in | Organic & biomolecular chemistry Vol. 17; no. 9; pp. 2351 - 2355 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
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Royal Soc Chemistry
2019
Royal Society of Chemistry |
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| Abstract | A series of chiral heterocyclic biaryls with a pyridyl moiety were prepared in moderate to good yields with up to 92% ee
via
asymmetric Suzuki–Miyaura coupling. The chiral-bridged biphenyl monophosphine ligand
L1
was found to be much more effective in the reaction enantioselection than its counterpart binaphthyl monophosphine ligands. |
|---|---|
| AbstractList | A series of chiral heterocyclic biaryls with a pyridyl moiety were prepared in moderate to good yields with up to 92% ee via asymmetric Suzuki-Miyaura coupling. The chiral-bridged biphenyl monophosphine ligand L1 was found to be much more effective in the reaction enantioselection than its counterpart binaphthyl monophosphine ligands. A series of chiral heterocyclic biaryls with a pyridyl moiety were prepared in moderate to good yields with up to 92% ee via asymmetric Suzuki-Miyaura coupling. The chiral-bridged biphenyl monophosphine ligand L1 was found to be much more effective in the reaction enantioselection than its counterpart binaphthyl monophosphine ligands.A series of chiral heterocyclic biaryls with a pyridyl moiety were prepared in moderate to good yields with up to 92% ee via asymmetric Suzuki-Miyaura coupling. The chiral-bridged biphenyl monophosphine ligand L1 was found to be much more effective in the reaction enantioselection than its counterpart binaphthyl monophosphine ligands. A series of chiral heterocyclic biaryls with a pyridyl moiety were prepared in moderate to good yields with up to 92% ee via asymmetric Suzuki–Miyaura coupling. The chiral-bridged biphenyl monophosphine ligand L1 was found to be much more effective in the reaction enantioselection than its counterpart binaphthyl monophosphine ligands. |
| Author | Zhang, Yaqi Xia, Wang Liang, Hao Li, Yongsu Jiang, Xiaoding Cao, Rihui Zhang, Zhen-Wei Qiu, Liqin |
| Author_xml | – sequence: 1 givenname: Wang surname: Xia fullname: Xia, Wang organization: School of Chemistry, The Key Laboratory of Low-carbon Chemistry & Energy Conservation of Guangdong Province, Guangdong Key Lab of Chiral Molecules and Drug Discovery, South China Sea Bio-Resource Exploitation and Utilization Collaborative Innovation Center, Sun Yat-Sen University – sequence: 2 givenname: Zhen-Wei surname: Zhang fullname: Zhang, Zhen-Wei organization: College of Pharmacy, Guangxi Zhuang-Yao Medicine Center of Engineering and Technology, Guangxi University of Chinese Medicine, Nanning, People's Republic of China – sequence: 3 givenname: Yongsu surname: Li fullname: Li, Yongsu organization: School of Chemistry, The Key Laboratory of Low-carbon Chemistry & Energy Conservation of Guangdong Province, Guangdong Key Lab of Chiral Molecules and Drug Discovery, South China Sea Bio-Resource Exploitation and Utilization Collaborative Innovation Center, Sun Yat-Sen University – sequence: 4 givenname: Xiaoding surname: Jiang fullname: Jiang, Xiaoding organization: School of Chemistry, The Key Laboratory of Low-carbon Chemistry & Energy Conservation of Guangdong Province, Guangdong Key Lab of Chiral Molecules and Drug Discovery, South China Sea Bio-Resource Exploitation and Utilization Collaborative Innovation Center, Sun Yat-Sen University – sequence: 5 givenname: Hao surname: Liang fullname: Liang, Hao organization: School of Chemistry, The Key Laboratory of Low-carbon Chemistry & Energy Conservation of Guangdong Province, Guangdong Key Lab of Chiral Molecules and Drug Discovery, South China Sea Bio-Resource Exploitation and Utilization Collaborative Innovation Center, Sun Yat-Sen University – sequence: 6 givenname: Yaqi surname: Zhang fullname: Zhang, Yaqi organization: School of Chemistry, The Key Laboratory of Low-carbon Chemistry & Energy Conservation of Guangdong Province, Guangdong Key Lab of Chiral Molecules and Drug Discovery, South China Sea Bio-Resource Exploitation and Utilization Collaborative Innovation Center, Sun Yat-Sen University – sequence: 7 givenname: Rihui surname: Cao fullname: Cao, Rihui organization: School of Chemistry, The Key Laboratory of Low-carbon Chemistry & Energy Conservation of Guangdong Province, Guangdong Key Lab of Chiral Molecules and Drug Discovery, South China Sea Bio-Resource Exploitation and Utilization Collaborative Innovation Center, Sun Yat-Sen University – sequence: 8 givenname: Liqin orcidid: 0000-0003-1703-3530 surname: Qiu fullname: Qiu, Liqin organization: School of Chemistry, The Key Laboratory of Low-carbon Chemistry & Energy Conservation of Guangdong Province, Guangdong Key Lab of Chiral Molecules and Drug Discovery, South China Sea Bio-Resource Exploitation and Utilization Collaborative Innovation Center, Sun Yat-Sen University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30758364$$D View this record in MEDLINE/PubMed |
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| CitedBy_id | crossref_primary_10_1016_j_poly_2024_116903 crossref_primary_10_1016_j_tetlet_2020_151784 crossref_primary_10_1021_acscatal_9b04354 crossref_primary_10_1021_acscatal_2c02090 crossref_primary_10_1002_chem_201905814 crossref_primary_10_1002_ejoc_202400995 crossref_primary_10_1016_j_tetlet_2024_155071 crossref_primary_10_1021_acscatal_2c00933 crossref_primary_10_1002_slct_201900980 |
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| Keywords | ATROPISOMERIC MONOPHOSPHINE LIGANDS EFFICIENT SYNTHESIS 1ST DIASTEREOSELECTIVE SYNTHESIS ARYL CHLORIDES |
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| Snippet | A series of chiral heterocyclic biaryls with a pyridyl moiety were prepared in moderate to good yields with up to 92% ee
via
asymmetric Suzuki–Miyaura... A series of chiral heterocyclic biaryls with a pyridyl moiety were prepared in moderate to good yields with up to 92% ee via asymmetric Suzuki-Miyaura... A series of chiral heterocyclic biaryls with a pyridyl moiety were prepared in moderate to good yields with up to 92% ee via asymmetric Suzuki–Miyaura... |
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| SubjectTerms | Biphenyl Chemistry Chemistry, Organic Cross coupling Enantiomers Ligands Physical Sciences Science & Technology |
| Title | Enantioselective synthesis of chiral heterocyclic biaryls via asymmetric Suzuki–Miyaura cross-coupling of 3-bromopyridine derivatives |
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