Manganese(I)-Catalyzed Direct Addition of C(sp3)-H Bonds to Aryl Isocyanates
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作者:
Liu, Hongxin
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机构:
Nankai Univ, Coll Chem, State Key Lab Elemento Organ Chem, Tianjin 300071, Peoples R ChinaNankai Univ, Coll Chem, State Key Lab Elemento Organ Chem, Tianjin 300071, Peoples R China
Liu, Hongxin
[1
]
Yu, Zhichao
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机构:
Nankai Univ, Coll Chem, State Key Lab Elemento Organ Chem, Tianjin 300071, Peoples R ChinaNankai Univ, Coll Chem, State Key Lab Elemento Organ Chem, Tianjin 300071, Peoples R China
Yu, Zhichao
[1
]
Li, Bin
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Nankai Univ, Coll Chem, State Key Lab Elemento Organ Chem, Tianjin 300071, Peoples R ChinaNankai Univ, Coll Chem, State Key Lab Elemento Organ Chem, Tianjin 300071, Peoples R China
Li, Bin
[1
]
Wang, Baiquan
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机构:
Nankai Univ, Coll Chem, State Key Lab Elemento Organ Chem, Tianjin 300071, Peoples R China
Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R ChinaNankai Univ, Coll Chem, State Key Lab Elemento Organ Chem, Tianjin 300071, Peoples R China
Wang, Baiquan
[1
,2
]
机构:
[1] Nankai Univ, Coll Chem, State Key Lab Elemento Organ Chem, Tianjin 300071, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
C-H BOND;
DIRECT NUCLEOPHILIC-ADDITION;
CYCLIZATION DIRECT SYNTHESIS;
CATALYZED DIRECT ADDITION;
HETEROAROMATIC-COMPOUNDS;
VERSATILE ROUTE;
ORTHO-AMIDATION;
MANGANESE;
ACTIVATION;
AMINOCARBONYLATION;
D O I:
10.1021/acs.joc.4c01581
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
The addition of C-H bonds to isocyanates catalyzed by transition metals is a highly auspicious methodology for providing synthetically and biologically important amides. However, the substrates are limited to C(sp(2))-H bonds. In this work, an efficient manganese(I)-catalyzed direct addition reaction of C(sp(3))-H bonds of 8-methylquinolines to aryl isocyanates has been developed, leading to the synthesis of various alpha-quinolinyl amide compounds in moderate to high yields. The reaction has a broad range of substrates and a good functional group tolerance. A possible mechanism is proposed based on the experimental results.
机构:
Tianjin Univ, Dept Chem, Tianjin Key Lab Mol Optoelect Sci, Tianjin 300072, Peoples R China
Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300072, Peoples R ChinaTianjin Univ, Dept Chem, Tianjin Key Lab Mol Optoelect Sci, Tianjin 300072, Peoples R China
Chen, Zhen
Rong, Meng-Yu
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机构:
Tianjin Univ, Dept Chem, Tianjin Key Lab Mol Optoelect Sci, Tianjin 300072, Peoples R China
Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300072, Peoples R ChinaTianjin Univ, Dept Chem, Tianjin Key Lab Mol Optoelect Sci, Tianjin 300072, Peoples R China
Rong, Meng-Yu
Nie, Jing
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机构:
Tianjin Univ, Dept Chem, Tianjin Key Lab Mol Optoelect Sci, Tianjin 300072, Peoples R China
Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300072, Peoples R ChinaTianjin Univ, Dept Chem, Tianjin Key Lab Mol Optoelect Sci, Tianjin 300072, Peoples R China
Nie, Jing
Zhu, Xue-Feng
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机构:
Novartis Res Fdn, Genom Inst, 10675 John Jay Hopkins Dr, San Diego, CA 92121 USATianjin Univ, Dept Chem, Tianjin Key Lab Mol Optoelect Sci, Tianjin 300072, Peoples R China
Zhu, Xue-Feng
Shi, Bing-Feng
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机构:
Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R ChinaTianjin Univ, Dept Chem, Tianjin Key Lab Mol Optoelect Sci, Tianjin 300072, Peoples R China
Shi, Bing-Feng
Ma, Jun-An
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机构:
Tianjin Univ, Dept Chem, Tianjin Key Lab Mol Optoelect Sci, Tianjin 300072, Peoples R China
Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300072, Peoples R ChinaTianjin Univ, Dept Chem, Tianjin Key Lab Mol Optoelect Sci, Tianjin 300072, Peoples R China