Platinum(II)-Catalyzed Ethylene Hydrophenylation: Switching Selectivity between Alkyl- and Vinylbenzene Production

被引：33

作者：

McKeown, Bradley A. ^{[1
]}

Gonzalez, H. Emanuel ^{[2
]}

Friedfeld, Max R. ^{[1
]}

Brosnahan, Anna M. ^{[1
]}

Gunnoe, T. Brent ^{[1
]}

Cundari, Thomas R. ^{[2
]}

Sabat, Michal ^{[3
]}

机构：

[1] Univ Virginia, Dept Chem, Charlottesville, VA 22904 USA

[2] Univ N Texas, Dept Chem, Ctr Adv Sci Comp & Modeling CASCaM, Denton, TX 76203 USA

[3] Univ Virginia, Mat Sci & Engn Dept, Nanoscale Mat Characterizat Facil, Charlottesville, VA 22904 USA

来源：

ORGANOMETALLICS | 2013年 / 32卷 / 09期

基金：

美国国家科学基金会;

关键词：

C-H BOND; ASYMMETRIC HYDROGENATION; CATALYTIC HYDROARYLATION; ACTIVATION; COMPLEXES; OLEFINS; FUNCTIONALIZATION; TPRU(L)(NCME)PH; MECHANISM; ARYLATION;

D O I：

10.1021/om400306w

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The series of Pt-II complexes [((x)bpy)Pt(Ph)(THF)][BAr'(4)] ((x)bpy=4,4'-X-2,2'-bipyridyl, X = OMe, Bu-t, H, Br, CO2Et, NO2; Ar' = 3,5-bis(trifluoromethyl)phenyl) are catalyst precursors for ethylene hydrophenylation. The bipyridyl substituent provides a tunable switch for catalyst selectivity that also has significant influence on catalyst activity and longevity. Less electron donating 4,4'-substituents increase the propensity toward styrene formation over ethylbenzene.

引用

页码：2857 / 2865

页数：9

共 47 条

[1] ORGANOPLATINUM(IV) POLYMERS AND MODEL COMPLEXES BY OXIDATIVE ADDITION OF BROMOACETATE ESTERS
ACHAR, S
SCOTT, JD
VITTAL, JJ
PUDDEPHATT, RJ
[J]. ORGANOMETALLICS, 1993, 12 (11) : 4592 - 4598
[2] Transition metal catalyzed hydroarylation of olefins using unactivated substrates: Recent developments and challenges
Andreatta, Jeremy R.
McKeown, Bradley A.
Gunnoe, T. Brent
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (01) : 305 - 315
[3] C-H Bond Activation in Transition Metal Species from a Computational Perspective
Balcells, David
Clot, Eric
Eisenstein, Odile
[J]. CHEMICAL REVIEWS, 2010, 110 (02) : 749 - 823
[4] New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction
Bandini, M
Melloni, A
Umani-Ronchi, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (05) : 550 - 556
[5] The heck reaction as a sharpening stone of palladium catalysis
Beletskaya, IP
Cheprakov, AV
[J]. CHEMICAL REVIEWS, 2000, 100 (08) : 3009 - 3066
[6] Mechanism of efficient anti-Markovnikov olefin hydroarylation catalyzed by homogeneous Ir(III) complexes
Bhalla, Gaurav
Bischof, Steven M.
Ganesh, Somesh K.
Liu, Xiang Yang
Jones, C. J.
Borzenko, Andrey
Tenn, William J., III
Ess, Daniel H.
Hashiguchi, Brian G.
Lokare, Kapil S.
Leung, Chin Hin
Oxgaard, Jonas
Goddard, William A., III
Periana, Roy A.
[J]. GREEN CHEMISTRY, 2011, 13 (01) : 69 - 81
[7] [(3,5-(CF3)2C6H3)4B]-[H(OET2)2]+ - A CONVENIENT REAGENT FOR GENERATION AND STABILIZATION OF CATIONIC, HIGHLY ELECTROPHILIC ORGANOMETALLIC COMPLEXES
BROOKHART, M
GRANT, B
VOLPE, AF
[J]. ORGANOMETALLICS, 1992, 11 (11) : 3920 - 3922
[8] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality
Chen, Xiao
Engle, Keary M.
Wang, Dong-Hui
Yu, Jin-Quan
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) : 5094 - 5115
[9] Palladium-catalyzed C-H functionalization of pyridine N-oxides:: Highly selective alkenylation and direct arylation with unactivated arenes
Cho, Seung Hwan
Hwang, Seung Jun
Chang, Sukbok
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) : 9254 - +
[10] Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation
Colby, Denise A.
Bergman, Robert G.
Ellman, Jonathan A.
[J]. CHEMICAL REVIEWS, 2010, 110 (02) : 624 - 655

← 1 2 3 4 5 →