Copper-promoted direct C-H alkoxylation of S,S-functionalized internal olefins with alcohols

被引：23

作者：

Liu, Zhuqing ^{[1
,2
]}

Huang, Fei ^{[1
,2
]}

Lou, Jiang ^{[1
,2
]}

Wang, Quannan ^{[1
,2
]}

Yu, Zhengkun ^{[1
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, 457 Zhongshan Rd, Dalian 116023, Liaoning, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 26期

关键词：

O BOND FORMATION; OXO KETENE DITHIOACETALS; ARYL ETHERS; UNACTIVATED C(SP(3))-H; EFFICIENT SYNTHESIS; CATALYZED ETHERIFICATION; C(SP(2))-H BONDS; ENOL ETHERS; FUNCTIONALIZATION; ACTIVATION;

D O I：

10.1039/c7ob01234a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper-promoted direct C-H alkoxylation of S, S-functionalized internal olefins, that is, alpha-oxo ketene dithioacetals, was efficiently achieved with alcohols as the alkoxylating agents, (diacetoxyiodo)benzene (PhI(OAc)(2)) as the oxidant, and benzoquinone (BQ) as the co-oxidant. The alkoxylated olefins were thus constructed and applied for the synthesis of alkoxylated N-heterocycles. The polarization of the olefinic carbon-carbon double bond by the electron-donating dialkylthio and electron-withdrawing alpha-oxo functionalities plays a crucial role in making such C-H alkoxylation reactions to occur under mild conditions. Mechanistic studies implicate a single-electron-transfer (SET) reaction pathway involved in the overall catalytic cycle.

引用

页码：5535 / 5540

页数：6

共 55 条

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