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

被引：5
作者：
Huang, Yi [1 ,2 ]
Lv, Xiaoyan [1 ,2 ]
Tong, Hua-Rong [1 ,2 ]
He, Wenji [1 ,2 ]
Bai, Ziqian [1 ,2 ]
Wang, Hao [1 ,2 ]
He, Gang [1 ,2 ]
Chen, Gong [1 ,2 ,3 ,4 ]
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
来源：
ORGANIC LETTERS | 2023年 / 26卷 / 01期
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.
引用
收藏
页码：94 / 99
页数：6
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