Versatile and highly efficient oxidative C(sp3)–H bond functionalization of tetrahydroisoquinoline promoted by bifunctional diethyl azodicarboxylate (DEAD): scope and mechanistic insights‡

文献情報

出版日 2016-08-01

DOI 10.1039/C6QO00249H

インパクトファクター 5.281

著者

Takuya Suga, Sunao Iizuka, Takahiko Akiyama

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要旨

Oxidative C(sp3)–H bond functionalization of the 1-position of tetrahydroisoquinoline (THIQ) derivatives was performed by using diethyl azodicarboxylate (DEAD) as the oxidant. A wide range of nucleophiles, including ketene silyl acetal, silyl enol ether, nitroalkane, dimethyl malonate, terminal alkyne, ketone, phosphonate, trimethylsilyl cyanide, and allylstannane gave very high yields without their excessive use. A mechanistic study revealed that the oxidative and basic nature of DEAD is responsible for its high efficiency.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Versatile and highly efficient oxidative C(sp3)–H bond functionalization of tetrahydroisoquinoline promoted by bifunctional diethyl azodicarboxylate (DEAD): scope and mechanistic insights‡

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