Selective Late-Stage Hydrodefluorination of Trifluoromethylarenes: A Facile Access to Difluoromethylarenes

被引：75

作者：

Munoz, Socrates B. ^{[1
,2
]}

Ni, Chuanfa ^{[3
]}

Zhang, Zhe ^{[1
,2
]}

Wang, Fang ^{[1
,2
]}

Shao, Nan ^{[1
,2
]}

Mathew, Thomas ^{[1
,2
]}

Olah, George A. ^{[1
,2
]}

Prakash, G. K. Surya ^{[1
,2
]}

机构：

[1] Univ Southern Calif, Loker Hydrocarbon Res Inst, Univ Pk, Los Angeles, CA 90089 USA

[2] Univ Southern Calif, Dept Chem, Univ Pk, Los Angeles, CA 90089 USA

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Ling Ling Rd, Shanghai 200032, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 16期

关键词：

Fluorine; Magnesium; C-F bond activation; Late-stage functionalization; Synthetic methods; Fluorinated compounds; F BOND ACTIVATION; COPPER-MEDIATED DIFLUOROMETHYLATION; CISPLATIN-INDUCED EMESIS; ROOM-TEMPERATURE; CATALYTIC HYDRODEFLUORINATION; (DIFLUOROMETHYL)ZINC REAGENT; FLUORINATED MOLECULES; RECEPTOR ANTAGONIST; COUPLING REACTION; C(SP(3))-F BONDS;

D O I：

10.1002/ejoc.201700396

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A selective reductive monodefluorination reaction of trifluoromethyl arenes was developed. Mediated by magnesium metal, various difluoromethylated aromatics were accessed at room temperature in the presence of acetic acid. This protocol shows tolerance to a wide range of functional groups and it was applicable in late-stage hydrodefluorination of complex pharmaceutical compounds, affording the corresponding CF2H analogues and their deuterated (CF2D) counterparts.

引用

页码：2322 / 2326

页数：5

共 97 条

[1]

Ahrens M., 2013, ANGEW CHEM, V125, P5436

[2] Catalytic Hydrodefluorination of Fluoromethanes at Room Temperature by Silylium-ion-like Surface Species [J].