Cyclopentadiene-mediated hydride transfer from rhodium complexes

被引:150
作者
Pitman, C. L. [1 ]
Finster, O. N. L. [1 ]
Miller, A. J. M. [1 ]
机构
[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA
基金
美国国家科学基金会;
关键词
1,4-NADH DERIVATIVES; ORGANIC-SYNTHESIS; REDUCTION; REGENERATION; CATALYSTS; WATER; REACTIVITY; HYDRICITY; CHEMISTRY; COFACTORS;
D O I
10.1039/c6cc00575f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Attempts to generate a proposed rhodium hydride catalytic intermediate instead resulted in isolation of (Cp*H)Rh(bpy)Cl (1), a pentamethylcyclopentadiene complex, formed by C-H bond-forming reductive elimination from the fleeting rhodium hydride. The hydride transfer ability of diene 1 was explored through thermochemistry and hydride transfer reactions, including the reduction of NAD(+).
引用
收藏
页码:9105 / 9108
页数:4
相关论文
共 33 条
[1]   Isolation and crystal structure of a water-soluble iridium hydride: A robust and highly active catalyst for acid-catalyzed transfer hydrogenations of carbonyl compounds in acidic media [J].
Abura, T ;
Ogo, S ;
Watanabe, Y ;
Fukuzumi, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (14) :4149-4154
[2]  
Aguirre Quintana L. M. A., UNPUB
[3]   Pentamethylcyclopentadienyl rhodium complexes [J].
Blakemore, James D. ;
Hernandez, Emilia S. ;
Sattler, Wesley ;
Hunter, Bryan M. ;
Henling, Lawrence M. ;
Brunschwig, Bruce S. ;
Gray, Harry B. .
POLYHEDRON, 2014, 84 :14-18
[4]   Mechanistic insights into an unprecedented C-C bond activation on a Rh/Ga bimetallic complex: A combined experimental/computational approach [J].
Cadenbach, T ;
Gemel, C ;
Schmid, R ;
Fischer, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (48) :17068-17078
[5]   REGENERATION OF NICOTINAMIDE COFACTORS FOR USE IN ORGANIC-SYNTHESIS [J].
CHENAULT, HK ;
WHITESIDES, GM .
APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY, 1987, 14 (02) :147-197
[6]   Counterion-dependent deuteration of pentamethylcyclopentadiene in water-soluble cationic Rh(III) complexes assisted by PTA [J].
Ciancaleoni, Gianluca ;
Bolano, Sandra ;
Bravo, Jorge ;
Peruzzini, Maurizio ;
Gonsalvi, Luca ;
Macchioni, Alceo .
DALTON TRANSACTIONS, 2010, 39 (14) :3366-3368
[7]   Predicting the reactivity of hydride donors in water: thermodynamic constants for hydrogen [J].
Connelly, Samantha J. ;
Wiedner, Eric S. ;
Appel, Aaron M. .
DALTON TRANSACTIONS, 2015, 44 (13) :5933-5938
[8]   Hydricities of d6 Metal Hydride Complexes in Water [J].
Creutz, Carol ;
Chou, Mei H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (08) :2794-+
[9]   ENZYMES IN ORGANIC-SYNTHESIS - OXIDOREDUCTIONS [J].
FANG, JM ;
LIN, CH ;
BRADSHAW, CW ;
WONG, CH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (08) :967-978
[10]   Visible light photocatalytic reduction of aldehydes by Rh(III)-H: a detailed mechanistic study [J].
Ghosh, T. ;
Slanina, T. ;
Koenig, B. .
CHEMICAL SCIENCE, 2015, 6 (03) :2027-2034