Palladium-Catalyzed Highly Regioselective Aromatic Substitution of Benzylic Ammonium Salts with Amines

被引：19

作者：

Xu, Ya-Nan ^{[1
,2
]}

Zhu, Meng-Zeng ^{[1
,2
]}

Lin, Yu-Kun ^{[1
,2
]}

Tian, Shi-Kai ^{[1
,2
,3
]}

机构：

[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Ctr Excellence Mol Synth, Hefei 230026, Anhui, Peoples R China

[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 17期

基金：

中国国家自然科学基金;

关键词：

IN-SITU ACTIVATION; C-N BONDS; BORONIC ACIDS; CROSS-COUPLINGS; BENZYLTRIMETHYLAMMONIUM SALTS; ARYLTRIMETHYLAMMONIUM IODIDES; STEREOSELECTIVE-SYNTHESIS; BENZYLAMMONIUM SALTS; GRIGNARD-REAGENTS; H BONDS;

D O I：

10.1021/acs.orglett.9b02820

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unprecedented aromatic substitution reaction of benzylic ammonium salts has been developed through palladium-catalyzed C-N bond cleavage. A range of primary and secondary amines participated in a palladium-catalyzed aromatic substitution reaction of benzylic ammonium salts, delivering sterically hindered aromatic amines in moderate to excellent yields with extremely high regioselectivity. Preliminary mechanistic studies permitted successful identification of pi-benzylpalladium complexes and gamma-vinyl allylic amines as key intermediates. This study paves the way for the use of benzylic ammonium salts in the aromatic substitution reactions.

引用

页码：7169 / 7173

页数：5

共 80 条

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