Copper-Catalyzed C-H Fluorination/Functionalization Sequence Enabling Benzylic C-H Cross Coupling with Diverse Nucleophiles

被引:79
作者
Vasilopoulos, Aristidis [1 ]
Golden, Dung L. [1 ]
Buss, Joshua A. [1 ]
Stahl, Shannon S. [1 ]
机构
[1] Univ Wisconsin, Dept Chem, 1101 Univ Ave, Madison, WI 53706 USA
关键词
BONDS; ACTIVATION; AMINATION; FUNCTIONALIZATION;
D O I
10.1021/acs.orglett.0c02238
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Site-selective transformation of benzylic C-H bonds into diverse functional groups is achieved via Cu-catalyzed C-H fluorination with N-fluorobenzenesulfonimide (NFSI), followed by substitution of the resulting fluoride with various nucleophiles. The benzyl fluorides generated in these reactions are reactive electrophiles in the presence of hydrogen-bond donors or Lewis acids, allowing them to be used without isolation in C-O, C-N, and C-C coupling reactions.
引用
收藏
页码:5753 / 5757
页数:5
相关论文
共 46 条
[1]   C-F Bond Activation in Organic Synthesis [J].
Amii, Hideki ;
Uneyama, Kenji .
CHEMICAL REVIEWS, 2009, 109 (05) :2119-2183
[2]  
Bakhoda A., 2019, ANGEW CHEM INT EDIT, V58, P3421
[3]   THE PREPARATION AND PROPERTIES OF SOME SUBSTITUTED BENZYL FLUORIDES [J].
BERNSTEIN, J ;
ROTH, JS ;
MILLER, WT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (07) :2310-2314
[4]   Organic synthesis provides opportunities to transform drug discovery [J].
Blakemore, David C. ;
Castro, Luis ;
Churcher, Ian ;
Rees, David C. ;
Thomas, Andrew W. ;
Wilson, David M. ;
Wood, Anthony .
NATURE CHEMISTRY, 2018, 10 (04) :383-394
[5]   Palladium-Catalyzed Substitution and Cross-Coupling of Benzylic Fluorides [J].
Blessley, George ;
Holden, Patrick ;
Walker, Matthew ;
Brown, John M. ;
Gouverneur, Veronique .
ORGANIC LETTERS, 2012, 14 (11) :2754-2757
[6]   Iron(II)-Catalyzed Benzylic Fluorination [J].
Bloom, Steven ;
Pitts, Cody Ross ;
Woltornist, Ryan ;
Griswold, Andrew ;
Holl, Maxwell Gargiulo ;
Lectka, Thomas .
ORGANIC LETTERS, 2013, 15 (07) :1722-1724
[7]   Intermolecular Radical C(sp3)-H Amination under Iodine Catalysis [J].
Bosnidou, Alexandra E. ;
Muniz, Kilian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (22) :7485-7489
[8]   Analysis of Past and Present Synthetic Methodologies on Medicinal Chemistry: Where Have All the New Reactions Gone? [J].
Brow, Dean G. ;
Bostrom, Jonas .
JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (10) :4443-4458
[9]   Copper-Catalyzed Functionalization of Benzylic C-H Bonds with N-Fluorobenzenesulfonimide: Switch from C-N to C-F Bond Formation Promoted by a Redox Buffer and Bronsted Base [J].
Buss, Joshua A. ;
Vasilopoulos, Aristidis ;
Golden, Dung L. ;
Stahl, Shannon S. .
ORGANIC LETTERS, 2020, 22 (15) :5749-5752
[10]   The medicinal chemist's toolbox for late stage functionalization of drug-like molecules [J].
Cernak, Tim ;
Dykstra, Kevin D. ;
Tyagarajan, Sriram ;
Vachal, Petr ;
Krska, Shane W. .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (03) :546-576