C(sp3)-H functionalizations of light hydrocarbons using decatungstate photocatalysis in flow

被引：327

作者：

Laudadio, Gabriele ^{[1
]}

Deng, Yuchao ^{[1
,2
,3
]}

van der Wal, Klaas ^{[1
]}

Ravelli, Davide ^{[4
]}

Nuno, Manuel ^{[5
]}

Fagnoni, Maurizio ^{[4
]}

Guthrie, Duncan ^{[5
]}

Sun, Yuhan ^{[2
,3
]}

Noel, Timothy ^{[1
]}

机构：

[1] Eindhoven Univ Technol, Dept Chem Engn & Chem, Micro Flow Chem & Synthet Methodol, Eindhoven, Netherlands

[2] ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai, Peoples R China

[3] Chinese Acad Sci, Shanghai Adv Res Inst, Shanghai 201210, Peoples R China

[4] Univ Pavia, Dept Chem, PhotoGreen Lab, I-27100 Pavia, Italy

[5] Vapourtec, Bury St Edmunds IP28 6TS, Suffolk, England

来源：

SCIENCE | 2020年 / 369卷 / 6499期

关键词：

H BOND FUNCTIONALIZATION; ACTIVATION; REDUCTION; ACCEPTOR; METHANE; ANION;

D O I：

10.1126/science.abb4688

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：

Direct activation of gaseous hydrocarbons remains a major challenge for the chemistry community. Because of the intrinsic inertness of these compounds, harsh reaction conditions are typically required to enable C(sp(3))-H bond cleavage, barring potential applications in synthetic organic chemistry. Here, we report a general and mild strategy to activate C(sp(3))-H bonds in methane, ethane, propane, and isobutane through hydrogen atom transfer using inexpensive decatungstate as photocatalyst at room temperature. The corresponding carbon-centered radicals can be effectively trapped by a variety of Michael acceptors, leading to the corresponding hydroalkylated adducts in good isolated yields and high selectivity (38 examples).

引用

页码：92 / +

页数：116

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