Oxalyl Amide Assisted Palladium-Catalyzed Arylation of C(sp2)-H Bond at the δ Position

被引:57
作者
Han, Jian [1 ]
Liu, Pei [1 ]
Wang, Chao [1 ]
Wang, Qian [1 ]
Zhang, Jingyu [1 ]
Zhao, Yanwei [1 ]
Shi, Daqing [1 ]
Huang, Zhibin [1 ]
Zhao, Yingsheng [1 ]
机构
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H BONDS; EFFICIENT SYNTHESIS; C(SP(3))-H BONDS; DIRECTING GROUP; ALKYL; ARYL; CYCLIZATION; ACTIVATION; AMINATION; VERSATILE;
D O I
10.1021/ol502745g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A successful protocol has been developed for delta-arylation of beta-arylethamines at the ortho position under mild conditions. The newly developed methodology first presents broad substrate scope, great functional group tolerance, and good to excellent yield in the synthesis of substituted beta-arylethylamines. The transformation represents a practical advantage of oxalyl amide in assistance with CH functionalization at a remote position.
引用
收藏
页码:5682 / 5685
页数:4
相关论文
共 58 条
[1]   Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].
Ackermann, Lutz .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295
[2]   Nickel-Catalyzed Direct Alkylation of C-H Bonds in Benzamides and Acrylamides with Functionalized Alkyl Halides via Bidentate-Chelation Assistance [J].
Aihara, Yoshinori ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) :5308-5311
[3]   RIGID 5-MEMBERED AND 6-MEMBERED C,N,N'-BOUND ARYL, BENZYL, AND ALKYL ORGANOPALLADIUM COMPLEXES - SP(2) VS SP(3) C-H ACTIVATION DURING CYCLOPALLADATION AND PALLADIUM(IV) INTERMEDIATES IN OXIDATIVE ADDITION-REACTIONS WITH DIHALOGENS AND ALKYL-HALIDES [J].
ALSTERS, PL ;
ENGEL, PF ;
HOGERHEIDE, MP ;
COPIJN, M ;
SPEK, AL ;
VANKOTEN, G .
ORGANOMETALLICS, 1993, 12 (05) :1831-1844
[4]   Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation [J].
Cho, Seung Hwan ;
Kim, Ji Young ;
Kwak, Jaesung ;
Chang, Sukbok .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5068-5083
[5]   Rhodium Catalyzed Chelation-Assisted C-H Bond Functionalization Reactions [J].
Colby, Denise A. ;
Tsai, Andy S. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :814-825
[6]   Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].
Colby, Denise A. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
CHEMICAL REVIEWS, 2010, 110 (02) :624-655
[7]   Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds [J].
Daugulis, Olafs ;
Do, Hien-Quang ;
Shabashov, Dmitry .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (08) :1074-1086
[8]   Synthetic and Mechanistic Studies of Pd-Catalyzed C-H Arylation with Diaryliodonium Salts: Evidence for a Bimetallic High Oxidation State Pd Intermediate [J].
Deprez, Nicholas R. ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (31) :11234-11241
[9]   Insights into directing group ability in palladium-catalyzed C-H bond functionalization [J].
Desai, Lopa V. ;
Stowers, Kara J. ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (40) :13285-13293
[10]   The potential of palladacycles: More than just precatalysts [J].
Dupont, J ;
Consorti, CS ;
Spencer, J .
CHEMICAL REVIEWS, 2005, 105 (06) :2527-2571