C-Alkylation of N-alkylamides with styrenes in air and scale-up using a microwave flow reactor

被引：23

作者：

Barham, Joshua P. ^{[1
,2
]}

Tamaoki, Souma ^{[1
]}

Egami, Hiromichi ^{[1
]}

Ohneda, Noriyuki ^{[2
]}

Okamoto, Tadashi ^{[2
]}

Odajima, Hiromichi ^{[2
]}

Hamashima, Yoshitaka ^{[1
]}

机构：

[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, 52-1 Yada, Shizuoka, Shizuoka 4228526, Japan

[2] SAIDA FDS INC, 143-10 Isshiki, Yaizu, Shizuoka 4250054, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 41期

关键词：

BASE-CATALYZED REACTIONS; POTASSIUM TERT-BUTOXIDE; AMIDE BOND FORMATION; CARBOXYLIC-ACIDS; 1,4-ADDITION REACTIONS; AMIDATION; ADDITIONS; OLEFINS; AMINES;

D O I：

10.1039/c8ob02282h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

C-Alkylation of N-alkylamides with styrenes is reported, proceeding in ambient air/moisture to give arylbutanamides and pharmaceutically-relevant scaffolds in excellent mass balance. Various amide and styrene derivatives were tolerated, rapidly affording molecular complexity in a single step; thus highlighting the future utility of this transformation in the synthetic chemistry toolbox. Reaction scalability (up to 65 g h(-1) product) was demonstrated using a Microwave Flow reactor, as the first example of a C-alkylation reaction using styrenes in continuous flow.

引用

页码：7568 / 7573

页数：6

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