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Synthetic and mechanistic studies of...

Kwon, Ki Hyeok.

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Synthetic and mechanistic studies of coupling reactions involving Carbon-Hydrogen bond activation.

Record Type:	Language materials, printed : Monograph/item
Title/Author:	Synthetic and mechanistic studies of coupling reactions involving Carbon-Hydrogen bond activation./
Author:	Kwon, Ki Hyeok.
Description:	237 p.
Notes:	Source: Dissertation Abstracts International, Volume: 72-07, Section: B, page: 4034.
Contained By:	Dissertation Abstracts International72-07B.
Subject:	Chemistry, Organic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3454257
ISBN:	9781124632193

Synthetic and mechanistic studies of coupling reactions involving Carbon-Hydrogen bond activation.
Kwon, Ki Hyeok.

Synthetic and mechanistic studies of coupling reactions involving Carbon-Hydrogen bond activation. - 237 p.

Source: Dissertation Abstracts International, Volume: 72-07, Section: B, page: 4034.

Thesis (Ph.D.)--Marquette University, 2011.

Transition metal-catalyzed C-C bond forming reactions involving C-H bond activation have been shown to be effective methods for functionalization of unreactive compounds. Since Murai's pioneering work on ruthenium-catalyzed regioselective arene-to-alkene coupling reactions, a number of well-defined, late transition metal catalysts have been shown to mediate regioseletive C-C bond forming reaction involving C-H bond activation. Recently, late transition metal complexes have also been found to catalyze the regioselective coupling reaction of nitrogen containing compounds with alkenes as well as sp 3 bond insertions and oxidative coupling reaction of aimdes. The catalytic C-C bond forming reaction involving C-H bond activation would provide simple and atom economic pathways for making functionalized molecules. Although there are many examples of stoichiometric reaction of aromatic C-H bond activation with transition metal compounds, catalytic C-H bond activation reactions via catalytic system have been rarely employed in organic synthesis.

ISBN: 9781124632193Subjects--Topical Terms:

516206
Chemistry, Organic.

Synthetic and mechanistic studies of coupling reactions involving Carbon-Hydrogen bond activation.
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020 $a 9781124632193
035 $a (MiAaPQ)AAI3454257
035 $a AAI3454257
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100 1 $a Kwon, Ki Hyeok. $3 2094034
245 1 0 $a Synthetic and mechanistic studies of coupling reactions involving Carbon-Hydrogen bond activation.
300 $a 237 p.
500 $a Source: Dissertation Abstracts International, Volume: 72-07, Section: B, page: 4034.
500 $a Adviser: Chae S. Yi.
502 $a Thesis (Ph.D.)--Marquette University, 2011.
520 $a Transition metal-catalyzed C-C bond forming reactions involving C-H bond activation have been shown to be effective methods for functionalization of unreactive compounds. Since Murai's pioneering work on ruthenium-catalyzed regioselective arene-to-alkene coupling reactions, a number of well-defined, late transition metal catalysts have been shown to mediate regioseletive C-C bond forming reaction involving C-H bond activation. Recently, late transition metal complexes have also been found to catalyze the regioselective coupling reaction of nitrogen containing compounds with alkenes as well as sp 3 bond insertions and oxidative coupling reaction of aimdes. The catalytic C-C bond forming reaction involving C-H bond activation would provide simple and atom economic pathways for making functionalized molecules. Although there are many examples of stoichiometric reaction of aromatic C-H bond activation with transition metal compounds, catalytic C-H bond activation reactions via catalytic system have been rarely employed in organic synthesis.
520 $a An efficient catalytic conjugate addition reaction protocol has been developed for the synthesis of tetrasubstituted olefin products. The cationic ruthenium-hydride complex was found to be an effective catalyst for coupling reaction with alpha,beta-unsaturated carbonyl compounds and simple alkenes. The kinetic and spectroscopic data are consistent with three different mechanistic pathways depending on substrate employed. The reaction of an alpha,beta-unsaturated carbonyl compounds with simple olefins predominantly gave the tetrasubstituted olefin products. The mechanistic studies suggest that the olefin insertion into an alpha,beta-unsaturated carbonyl substrate is the rate-limiting step for conjugate addition reaction. On the other hand, the coupling reaction of alpha-methyl alpha,beta-unsaturated cinnamide with aromatic alkenes gave oxidative coupling products. The kinetic and spectroscopic studies support the different mechanistic pathway, which involves the rate-limiting vinyl C-H activation step, in comparison with the conjugate addition reaction. This synthetic methodology promises to provide a straightforward route to the valuable organic compounds such as tetrasubstituted olefins which are difficult to synthesize by using traditional synthetic methods.
590 $a School code: 0116.
650 4 $a Chemistry, Organic. $3 516206
650 4 $a Chemistry, Inorganic. $3 517253
690 $a 0490
690 $a 0488
710 2 $a Marquette University. $b Chemistry. $3 2092037
773 0 $t Dissertation Abstracts International $g 72-07B.
790 $a 0116
791 $a Ph.D.
792 $a 2011
793 $a English
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3454257