Highly efficient catalytic system for C-H activation: A practical approach to angiotensin II receptor blockers

ACS Catalysis

Volumn 1, Issue 6, 2011, Pages 607-610

  Seki, Masahiko ^a  

^a API Corporation   (Japan)

Author keywords

biaryls; C H activation; cross coupling; green chemistry; ruthenium

Indexed keywords

ANGIOTENSIN II; BIARYLS; C-H ACTIVATION; CATALYTIC SYSTEM; CROSS-COUPLINGS; GREEN CHEMISTRY;

ORGANOMETALLICS; RUTHENIUM; RUTHENIUM COMPOUNDS;

ACTIVATION ANALYSIS;

EID: 79958192763     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs200044t     Document Type: Article

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60. 2O with phosphine ligands have been reported in different types of reactions such as a hydroarylation employing ketones as the substrate. (31)
61. Lower catalyst loadings were reported employing Pd catalyst. (42, 50) However, they need expensive phosphine ligands.
62. Clarification of the role of water in the reaction needs further investigation. It may act as an effective ligand in the transient Ru complex or may facilitate the dissolution of the Ru complex in NMP.
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64. In the case of a hydroarylation employing ketones as the substrate, better results were reported by the use of phosphines bearing an electron-withdrawing group. (31)
65. The Pd/C catalysts tested in this study have two types of Pd distribution: egg shell and thick shell. In the egg shell type catalyst, Pd distributes close to the surface within 50-150 nm depth. The thick shell type catalyst denotes the one whose Pd distributes until 200-500 nm from the surface.
66. The use of 2b as the substrate increases the atom efficiency (8) by 170% compared to the previously employed 5-(2'-boronophenyl)-2-(triphenylmethyl)-2 H -tetrazole, a well documented substrate for the Suzuki coupling. (5)
67. 3 (2 equiv) at room temperature and then heating the mixture at 140 °C for 12 h resulted in a poor yield of 4b (42%). It may demonstrate that the transient Ru complex is unstable (active), and, to achieve a higher conversion, the substrates need to coexist with the active catalyst species formed in situ during the reaction.