Copper Catalyzed Oxidative Arylation of Tertiary Carbon Centers

被引:13
作者
Basnet, Prakash [1 ]
Sebold, Melissa B. [1 ]
Hendrick, Charles E. [1 ]
Kozlowski, Marisa C. [1 ]
机构
[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA
关键词
C-H BONDS; CHEMOSELECTIVE ACTIVATION; QUATERNARY STEREOCENTERS; IMINONITRILES; DIMERS; SP(3);
D O I
10.1021/acs.orglett.0c03581
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We describe herein a Cu(OTf)(2) catalyzed oxidative arylation of a tertiary carbon-containing substrate including aryl malononitriles, 3-aryl benzofuran-2-ones, and 3-aryl oxindoles. In some cases, the nitrile groups of the aryl malononitriles undergo further reactions leading to lactones or imines. These reaction conditions are applicable for a range of arenes, including phenols, anilines, anisoles, and heteroarenes. Mechanistic studies support the formation of a cationic intermediate via a two-electron oxidation.
引用
收藏
页码:9524 / 9528
页数:5
相关论文
共 44 条
[1]   THE KINETICS OF THE DECOMPOSITION OF POTASSIUM PERSULFATE IN AQUEOUS SOLUTIONS OF METHANOL [J].
BARTLETT, PD ;
COTMAN, JD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (04) :1419-1422
[2]   An organocatalytic oxidative coupling strategy for the direct synthesis of arylated quaternary stereogenic centers [J].
Bogle, Katherine M. ;
Hirst, David J. ;
Dixon, Darren J. .
ORGANIC LETTERS, 2007, 9 (23) :4901-4904
[3]   An oxidative coupling for the synthesis of arylated quaternary stereocentres and its application in the total synthesis of powelline and buphanidrine [J].
Bogle, Katherine M. ;
Hirst, David J. ;
Dixon, Darren J. .
TETRAHEDRON, 2010, 66 (33) :6399-6410
[4]   Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms [J].
Bueschleb, Martin ;
Dorich, Stephane ;
Hanessian, Stephen ;
Tao, Daniel ;
Schenthal, Kyle B. ;
Overman, Larry E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (13) :4156-4186
[5]   Spirotryprostatin B, a novel mammalian cell cycle inhibitor produced by Aspergillus fumigatus [J].
Cui, CB ;
Kakeya, H ;
Osada, H .
JOURNAL OF ANTIBIOTICS, 1996, 49 (08) :832-835
[6]   Chemoselective Activation of sp3 vs sp2 C-H Bonds with Pd(II) [J].
Curto, John M. ;
Kozlowski, Marisa C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (01) :18-21
[7]   OXIDATIVE CARBON-CARBON COUPLING .1. OXIDATIVE COUPLING OF ALPHA-SUBSTITUTED BENZYL CYANIDES [J].
DEJONGH, HAP ;
DEJONGE, CRH ;
MIJS, WJ .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (21) :3160-&
[8]   Nitrile-Containing Pharmaceuticals: Efficacious Roles of the Nitrile Pharmacophore [J].
Fleming, Fraser F. ;
Yao, Lihua ;
Ravikumar, P. C. ;
Funk, Lee ;
Shook, Brian C. .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (22) :7902-7917
[9]   One-pot three-component synthesis of α-iminonitriles by IBX/TBAB-Mediated oxidative Strecker reaction [J].
Fontaine, Patrice ;
Chiaroni, Angele ;
Masson, Geraldine ;
Zhu, Jieping .
ORGANIC LETTERS, 2008, 10 (08) :1509-1512
[10]   Bond dissociation energies for radical dimers derived from highly stabilized carbon-centered radicals [J].
Frenette, M ;
Aliaga, C ;
Font-Sanchis, E ;
Scaiano, JC .
ORGANIC LETTERS, 2004, 6 (15) :2579-2582