Investigations of the generality of quaternary ammonium salts as alkylating agents in direct C-H alkylation reactions: solid alternatives for gaseous olefins

被引：7

作者：

Schoenbauer, David ^{[1
]}

Spettel, Manuel ^{[1
]}

Pollice, Robert ^{[1
,2
]}

Pittenauer, Ernst ^{[3
]}

Schnuerch, Michael ^{[1
]}

机构：

[1] TU Wien, Inst Appl Synthet Chem, Getreidemarkt 9-163, A-1060 Vienna, Austria

[2] Swiss Fed Inst Technol, Dept Chem & Appl Biosci, Vladimir Prelog Weg 1-5-10, CH-8093 Zurich, Switzerland

[3] TU Wien, Inst Chem Technol & Analyt, Getreidemarkt 9-164, A-1060 Vienna, Austria

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 16期

关键词：

CATALYZED DIRECT ALKYLATION; METHYLENE C(SP(3))-H BONDS; CARBON-HYDROGEN BONDS; BENZYLIC AMINES; AROMATIC IMINES; FUNCTIONALIZATIONS; ARYLATION; REAGENTS; ETHYLENE; ALKENES;

D O I：

10.1039/c9ob00243j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

C-H alkylation reactions using short chain olefins as alkylating agents could be operationally simplified on the lab scale by using quaternary ammonium salts as precursors for these gaseous reagents: Hofmann elimination delivers in situ the desired alkenes with the advantage that the alkene concentration in the liquid phase is high. In case a catalytic system did not tolerate the conditions for Hofmann elimination, a very simple spatial separation of both reactions, Hofmann elimination and direct alkylation, was achieved to circumvent possible side reactions or catalyst deactivation. Additionally, the truly catalytically active species of a rhodium(I) mediated alkylation reaction could be identified by using this approach.

引用

页码：4024 / 4030

页数：7

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