C-H Functionalization at Sterically Congested Positions by the Platinum-Catalyzed Borylation of Arenes

被引:98
作者
Furukawa, Takayuki [1 ]
Tobisu, Mamoru [2 ,3 ]
Chatani, Naoto [1 ]
机构
[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
[2] Osaka Univ, Grad Sch Engn, Ctr Atom & Mol Technol, Suita, Osaka 5650871, Japan
[3] Kyoto Univ, ESICB, Kyoto 6158510, Japan
关键词
N-HETEROCYCLIC CARBENE; ARYL; COMPLEXES; BONDS; CONSTRUCTION; ACTIVATION; PALLADIUM; CHEMISTRY; MECHANISM; CLEAVAGE;
D O I
10.1021/jacs.5b07677
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Despite significant progress in the area of C-H bond functionalization of arenes, no general method has been reported for the functionalization of C-H bonds at the sterically encumbered positions of simple arenes, such as mesitylene. Herein, we report the development of the first platinum-based catalyst for C-H borylation of arenes and heteroarenes. Notably, this method exhibited high tolerance toward steric hindrance and provided rapid access to a series of 2,6-disubstituted phenylboronic esters, valuable building blocks for further elaborations.
引用
收藏
页码:12211 / 12214
页数:4
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共 59 条
[1]   Synthetic and structural studies of NHC-Pt(dvtms) complexes and their application as alkene hydrosilylation catalysts (NHC = N-heterocyclic carbene, dvtms = divinyltetramethylsiloxane) [J].
Berthon-Gelloz, G ;
Buisine, O ;
Brière, JF ;
Michaud, G ;
Stérin, S ;
Mignani, G ;
Tinant, B ;
Declercq, JP ;
Chapon, D ;
Markó, IE .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (24-25) :6156-6168
[2]   Mechanism of the mild functionalization of arenes by diboron reagents catalyzed by iridium complexes. Intermediacy and chemistry of bipyridine-ligated iridium trisboryl complexes [J].
Boller, TM ;
Murphy, JM ;
Hapke, M ;
Ishiyama, T ;
Miyaura, N ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (41) :14263-14278
[3]   Modern Carbon-Fluorine Bond Forming Reactions for Aryl Fluoride Synthesis [J].
Campbell, Michael G. ;
Ritter, Tobias .
CHEMICAL REVIEWS, 2015, 115 (02) :612-633
[4]   2-aryloxy-4-alkylaminopyridines: Discovery of novel corticotropin-releasing factor 1 antagonists [J].
Chen, Yuhpyng L. ;
Obach, R. Scott ;
Braselton, John ;
Corman, Michael L. ;
Forman, James ;
Freeman, Jody ;
Gallaschun, Randall J. ;
Mansbach, Robert ;
Schmidt, Anne W. ;
Sprouse, Jeffrey S. ;
Tingley, F. David, III ;
Winston, Elizabeth ;
Schulz, David W. .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (05) :1385-1392
[5]   Catalytic Silylation of Unactivated C-H Bonds [J].
Cheng, Chen ;
Hartwig, John F. .
CHEMICAL REVIEWS, 2015, 115 (17) :8946-8975
[6]   Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds [J].
Cho, JY ;
Tse, MK ;
Holmes, D ;
Maleczka, RE ;
Smith, MR .
SCIENCE, 2002, 295 (5553) :305-308
[7]   Sterically directed functionalization of aromatic C-H bonds: Selective borylation ortho to cyano groups in arenes and heterocycles [J].
Chotana, GA ;
Rak, MA ;
Smith, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (30) :10539-10544
[8]   Weakly Coordinating Directing Groups for Ruthenium(II)-Catalyzed C-H Activation [J].
De Sarkar, Suman ;
Liu, Weiping ;
Kozhushkov, Sergei I. ;
Ackermann, Lutz .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (07) :1461-1479
[9]   Iron-Catalyzed C-H Borylation of Arenes [J].
Dombray, Thomas ;
Werncke, C. Gunnar ;
Jiang, Shi ;
Grellier, Mary ;
Vendier, Laure ;
Bontemps, Sebastien ;
Sortais, Jean-Baptiste ;
Sabo-Etienne, Sylviane ;
Darcel, Christophe .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (12) :4062-4065
[10]   Synthesis, Structure, and Catalytic Studies of Palladium and Platinum Bis-Sulfoxide Complexes [J].
Drinkel, Emma E. ;
Wu, Linglin ;
Linden, Anthony ;
Dorta, Reto .
ORGANOMETALLICS, 2014, 33 (03) :627-636