N,N-Chelate-control on the regioselectivity in acetate-assisted C-H activation

被引:33
作者
Cross, Warren B. [1 ]
Hope, Eric G. [1 ]
Lin, Yi-Hsien [1 ]
Macgregor, Stuart A. [2 ]
Singh, Kuldip [1 ]
Solan, Gregory A. [1 ]
Yahya, Nurhusna [1 ]
机构
[1] Univ Leicester, Dept Chem, Leicester LE1 7RH, Leics, England
[2] Heriot Watt Univ, Inst Chem Sci, Edinburgh EH14 4AS, Midlothian, Scotland
关键词
COMPLEXES; MECHANISM; CYCLOPALLADATION; BOND; KINETICS; CYCLOMETALATION; POLYMERIZATION; PRECATALYSTS; PALLADATION; ARYLATION;
D O I
10.1039/c3cc38697j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Bidentate N,N-pyridylimine or N,N-pyridylamine donors are effective chelating ligands for regiospecific C-H activation at the peri-(C-8)-position of a naphthyl ring on reaction with palladium(II) acetate; DFT calculations show N,N-chelates bias the cyclopalladation towards 6-membered ring products.
引用
收藏
页码:1918 / 1920
页数:3
相关论文
共 33 条
[11]   Proton-abstraction mechanism in the palladium-catalyzed intramolecular arylation:: Substituent effects [J].
Garcia-Cuadrado, Domingo ;
de Mendoza, Paula ;
Braga, Ataualpa A. C. ;
Maseras, Feliu ;
Echavarren, Antonio M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (21) :6880-6886
[12]   CYCLOMETALATION OF ARYLAZO COMPOUNDS .3. DETERMINATION OF THE CHELATE RING SIZE IN A PERI-PALLADATED 1-ARYLAZONAPHTHALENE BY N-15 NUCLEAR MAGNETIC-RESONANCE [J].
GEHRIG, K ;
HUGENTOBLER, M ;
KLAUS, AJ ;
RYS, P .
INORGANIC CHEMISTRY, 1982, 21 (06) :2493-2494
[13]   Solution behaviour, kinetics and mechanism of the acid-catalysed cyclopalladation of imines [J].
Gomez, M ;
Granell, J ;
Martinez, M .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1998, (01) :37-43
[14]   Variable-temperature and -pressure kinetics and mechanism of the cyclopalladation reaction of imines in aprotic solvent [J].
Gomez, M ;
Granell, J ;
Martinez, M .
ORGANOMETALLICS, 1997, 16 (12) :2539-2546
[15]   Facile interconversions between diastereomers of chloro-bridged palladium(II) dimers of orthometallated (+/-)-dimethyl[1-(1-naphthyl)ethyl]amine [J].
Hockless, DCR ;
Gugger, PA ;
Leung, PH ;
Mayadunne, RC ;
Pabel, M ;
Wild, SB .
TETRAHEDRON, 1997, 53 (11) :4083-4094
[16]   Nickel and cationic palladium complexes bearing (imino) pyridyl alcohol ligands: Synthesis, characterization and vinyl polymerization of norbornene [J].
Jie, Suyun ;
Ai, Pengfei ;
Zhou, Qimeng ;
Li, Bo-Geng .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (07) :1465-1473
[17]   Scope and selectivity in palladium-catalyzed directed C-H bond halogenation reactions [J].
Kalyani, Dipannita ;
Dick, Allison R. ;
Anani, Waseem Q. ;
Sanford, Melanie S. .
TETRAHEDRON, 2006, 62 (49) :11483-11498
[18]   Cyclopalladation of 1,1′-azonaphthalene (= di(naphthalen-1-yl)diazene):: Isolation and characterization of two isomeric complexes [J].
Kind, L ;
Klaus, AJ ;
Rys, P ;
Gramlich, V .
HELVETICA CHIMICA ACTA, 1998, 81 (02) :307-316
[19]   Palladium-catalyzed benzene arylation: Incorporation of catalytic pivalic acid as a proton shuttle and a key element in catalyst design [J].
Lafrance, Marc ;
Fagnou, Keith .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (51) :16496-16497
[20]   Cyclopalladated complexes of perylene imine: mononuclear complexes with five- or six-membered metallacycles [J].
Lentijo, Sergio ;
Miguel, Jesus A. ;
Espinet, Pablo .
DALTON TRANSACTIONS, 2011, 40 (29) :7602-7609