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Palladium-Catalyzed Enantioselective Directed C(sp3)-H Functionalization Using C5-Substituted 8-Aminoquinoline Auxiliaries
被引:4
作者:

Huang, Yi
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Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
Nankai Univ, Inst Elemento Organ Chem, Coll Chem, Tianjin 300071, Peoples R China Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China

Lv, Xiaoyan
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h-index: 0
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Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
Nankai Univ, Inst Elemento Organ Chem, Coll Chem, Tianjin 300071, Peoples R China Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China

Tong, Hua-Rong
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h-index: 0
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Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
Nankai Univ, Inst Elemento Organ Chem, Coll Chem, Tianjin 300071, Peoples R China Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China

He, Wenji
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Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
Nankai Univ, Inst Elemento Organ Chem, Coll Chem, Tianjin 300071, Peoples R China Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China

Bai, Ziqian
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Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
Nankai Univ, Inst Elemento Organ Chem, Coll Chem, Tianjin 300071, Peoples R China Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China

Wang, Hao
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Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
Nankai Univ, Inst Elemento Organ Chem, Coll Chem, Tianjin 300071, Peoples R China Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China

He, Gang
论文数: 0 引用数: 0
h-index: 0
机构:
Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
Nankai Univ, Inst Elemento Organ Chem, Coll Chem, Tianjin 300071, Peoples R China Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China

Chen, Gong
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h-index: 0
机构:
Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
Nankai Univ, Inst Elemento Organ Chem, Coll Chem, Tianjin 300071, Peoples R China
Nankai Univ, Frontiers Sci Ctr New Organ Matter, Tianjin 300071, Peoples R China
Haihe Lab Sustainable Chem Transformat, Tianjin 300192, Peoples R China Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
机构:
[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Inst Elemento Organ Chem, Coll Chem, Tianjin 300071, Peoples R China
[3] Nankai Univ, Frontiers Sci Ctr New Organ Matter, Tianjin 300071, Peoples R China
[4] Haihe Lab Sustainable Chem Transformat, Tianjin 300192, Peoples R China
基金:
中国国家自然科学基金;
国家重点研发计划;
关键词:
C-H BONDS;
UNACTIVATED C(SP(3))-H;
ASYMMETRIC FUNCTIONALIZATION;
C(SP(2))-H BONDS;
ARYLATION;
ALKOXYLATION;
BIDENTATE;
D O I:
10.1021/acs.orglett.3c03688
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
8-Aminoquinoline (AQ) has proven to be a highly effective bidentate directing group for palladium-catalyzed C-H functionalization reactions. However, enantiocontrol of AQ-directed C(sp(3))-H functionalization reactions has been challenging. Herein, a new protocol is presented for the Pd-catalyzed enantioselective arylation of unactivated beta C(sp(3))-H bonds of alkyl carboxamides with aryl iodides using a C-5-iodinated 8-aminoquinolines (IQ) auxiliary in conjugation with a BINOL ligand. Additionally, a C-5-aryl substituted 8-aminoquinoline auxiliary can facilitate enantioselective alkenylation and alkynylation of benzylic C(sp(3))-H bonds of 3-arylpropanamides with the corresponding bromide reagents under similar conditions.
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页码:94 / 99
页数:6
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