One-pot aminobenzylation of aldehydes with toluenes

被引：76

作者：

Wang, Zhiting ^{[1
]}

Zheng, Zhipeng ^{[2
]}

Xu, Xinyu ^{[1
]}

Mao, Jianyou ^{[1
]}

Walsh, Patrick J. ^{[1
,2
]}

机构：

[1] Nanjing Tech Univ, Inst Adv Synth, Sch Chem & Mol Engn, Jiangsu Natl Synerget Innovat Ctr Adv Mat, 30 South Puzhu Rd, Nanjing 211816, Jiangsu, Peoples R China

[2] Univ Penn, Roy & Diana Vagelos Labs, Penn Merck Lab High Throughput Experimentat, Dept Chem, 231 South 34th St, Philadelphia, PA 19104 USA

来源：

NATURE COMMUNICATIONS | 2018年 / 9卷

基金：

美国国家科学基金会;

关键词：

C-H BONDS; TRANSIENT DIRECTING GROUP; DIARYLMETHANE PRONUCLEOPHILES; AROMATIC HETEROCYCLES; DIMETHYL-SULFOXIDE; C(SP(3))-H BONDS; ARYLATION; ACTIVATION; COMPLEXES; ACIDS;

D O I：

10.1038/s41467-018-05638-y

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Amines are fundamental motifs in bioactive natural products and pharmaceuticals. Using simple toluene derivatives, a one-pot aminobenzylation of aldehydes is introduced that provides rapid access to amines. Simply combining benzaldehydes, toluenes, NaN(SiMe3)(2), and additive Cs(O2CCF3) (0.35 equiv.) generates a diverse array of 1,2-diarylethylamine derivatives (36 examples, 56-98% yield). Furthermore, suitably functionalized 1,2-diarylethylamines were transformed into 2-aryl-substituted indoline derivatives via Buchwald-Hartwig amination. It is proposed that the successful deprotonation of toluene by MN(SiMe3)(2) is facilitated by cation-pi interactions between the arene and the group(I) cation that acidify the benzylic C-Hs.

引用

页数：8

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