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Catalytic intramolecular hydroarylat...

Thalji, Reema K.

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Catalytic intramolecular hydroarylation of alkenes via directed carbon-hydrogen bond activation.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Catalytic intramolecular hydroarylation of alkenes via directed carbon-hydrogen bond activation./
Author:	Thalji, Reema K.
Description:	169 p.
Notes:	Source: Dissertation Abstracts International, Volume: 65-09, Section: B, page: 4584.
Contained By:	Dissertation Abstracts International65-09B.
Subject:	Chemistry, Organic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3147030
ISBN:	0496055488

Catalytic intramolecular hydroarylation of alkenes via directed carbon-hydrogen bond activation.
Thalji, Reema K.

Catalytic intramolecular hydroarylation of alkenes via directed carbon-hydrogen bond activation. - 169 p.

Source: Dissertation Abstracts International, Volume: 65-09, Section: B, page: 4584.

Thesis (Ph.D.)--University of California, Berkeley, 2004.

In contemporary organic synthesis, one of the most attractive methods for carbon-carbon bond formation is the transition metal-catalyzed activation and functionalization of otherwise unreactive carbon-hydrogen bonds. Because C-H bonds are among the most ubiquitous and inexpensive chemical linkages in nature, the direct conversion of C-H bonds into C-C bonds represents an efficient and economical strategy for fine chemical production. For this reason, our group has been interested in developing intramolecular C-H activation/alkene insertion reactions that allow rapid access to synthetically useful compounds. This dissertation details our progress toward achieving this goal.

ISBN: 0496055488Subjects--Topical Terms:

516206
Chemistry, Organic.

Catalytic intramolecular hydroarylation of alkenes via directed carbon-hydrogen bond activation.
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100 1 $a Thalji, Reema K. $3 1939320
245 1 0 $a Catalytic intramolecular hydroarylation of alkenes via directed carbon-hydrogen bond activation.
300 $a 169 p.
500 $a Source: Dissertation Abstracts International, Volume: 65-09, Section: B, page: 4584.
500 $a Chair: Jonathan A. Ellman.
502 $a Thesis (Ph.D.)--University of California, Berkeley, 2004.
520 $a In contemporary organic synthesis, one of the most attractive methods for carbon-carbon bond formation is the transition metal-catalyzed activation and functionalization of otherwise unreactive carbon-hydrogen bonds. Because C-H bonds are among the most ubiquitous and inexpensive chemical linkages in nature, the direct conversion of C-H bonds into C-C bonds represents an efficient and economical strategy for fine chemical production. For this reason, our group has been interested in developing intramolecular C-H activation/alkene insertion reactions that allow rapid access to synthetically useful compounds. This dissertation details our progress toward achieving this goal.
520 $a Chapter 1 describes the annulation of aromatic ketones, in which the alkene is tethered at the meta position, which proceeds via ketone-directed C-H bond activation followed by alkene addition to the most hindered ortho site. Although this reaction is both efficient and highly selective, it requires the use of non-isomerizable Akenes, a limitation that can be overcome using imines instead of ketones. Chapter 2 describes the analogous cyclization reaction of aromatic ketimines and aldimines, which is tolerant of various functional groups, different tether lengths, a number of alkene substitution patterns, and the incorporation of heteroatoms in the tether, and which generally proceeds with high selectivity. The work in Chapter 2 constitutes a novel method for the synthesis of functionalized indanes, tetralanes, dihydrobenzofurans, dihydroindoles, and other polycyclic compounds from simple starting materials using directed C-H bond activation.
520 $a In spite of substantial recent research activity in the field of C-H activation, examples of catalytic enantioselective reactions involving this chemistry are rare. Chapter 3 details an enantioselective variant of the imine-directed C-H bond functionalization reaction. This work represents the first highly enantioselective catalytic reaction involving aromatic C-H bond activation. Moreover, the newly identified catalyst system enables the intramolecular alkylation reaction to proceed rapidly at temperatures 75°C lower than those required with the previously employed Wilkinson's catalyst.
590 $a School code: 0028.
650 4 $a Chemistry, Organic. $3 516206
650 4 $a Chemistry, Inorganic. $3 517253
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690 $a 0488
710 2 0 $a University of California, Berkeley. $3 687832
773 0 $t Dissertation Abstracts International $g 65-09B.
790 1 0 $a Ellman, Jonathan A., $e advisor
790 $a 0028
791 $a Ph.D.
792 $a 2004
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3147030