語系:
繁體中文
English
說明(常見問題)
回圖書館首頁
手機版館藏查詢
登入
回首頁
切換:
標籤
|
MARC模式
|
ISBD
Palladium-catalyzed C--C bond and C-...
~
Jia, Tiezheng.
FindBook
Google Book
Amazon
博客來
Palladium-catalyzed C--C bond and C--S bond forming reactions of sulfoxides.
紀錄類型:
書目-電子資源 : Monograph/item
正題名/作者:
Palladium-catalyzed C--C bond and C--S bond forming reactions of sulfoxides./
作者:
Jia, Tiezheng.
面頁冊數:
196 p.
附註:
Source: Dissertation Abstracts International, Volume: 76-11(E), Section: B.
Contained By:
Dissertation Abstracts International76-11B(E).
標題:
Analytical chemistry. -
電子資源:
http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3709485
ISBN:
9781321851144
Palladium-catalyzed C--C bond and C--S bond forming reactions of sulfoxides.
Jia, Tiezheng.
Palladium-catalyzed C--C bond and C--S bond forming reactions of sulfoxides.
- 196 p.
Source: Dissertation Abstracts International, Volume: 76-11(E), Section: B.
Thesis (Ph.D.)--University of Pennsylvania, 2015.
Transition metal catalyzed C-C bond and C-S bond forming reactions offer a new opportunity to construct sulfur-containing compounds. However, preparation of sulfoxides through this pathway remains sporadic, probably due to the very weakly acidic alpha-protons or instability of sulfenate anion, a key nucleophile to produce sulfoxides. To this end, this dissertation investigated the novel approaches to prepare sulfoxides via palladium catalyzed alpha-arylation of methyl sulfoxides and S-arylation of sulfenate anions.
ISBN: 9781321851144Subjects--Topical Terms:
3168300
Analytical chemistry.
Palladium-catalyzed C--C bond and C--S bond forming reactions of sulfoxides.
LDR
:03612nmm a2200313 4500
001
2067698
005
20160418090149.5
008
170521s2015 ||||||||||||||||| ||eng d
020
$a
9781321851144
035
$a
(MiAaPQ)AAI3709485
035
$a
AAI3709485
040
$a
MiAaPQ
$c
MiAaPQ
100
1
$a
Jia, Tiezheng.
$3
3182557
245
1 0
$a
Palladium-catalyzed C--C bond and C--S bond forming reactions of sulfoxides.
300
$a
196 p.
500
$a
Source: Dissertation Abstracts International, Volume: 76-11(E), Section: B.
500
$a
Adviser: Patrick J. Walsh.
502
$a
Thesis (Ph.D.)--University of Pennsylvania, 2015.
520
$a
Transition metal catalyzed C-C bond and C-S bond forming reactions offer a new opportunity to construct sulfur-containing compounds. However, preparation of sulfoxides through this pathway remains sporadic, probably due to the very weakly acidic alpha-protons or instability of sulfenate anion, a key nucleophile to produce sulfoxides. To this end, this dissertation investigated the novel approaches to prepare sulfoxides via palladium catalyzed alpha-arylation of methyl sulfoxides and S-arylation of sulfenate anions.
520
$a
In chapter 1, the palladium catalyzed alpha-arylation of unactivated sulfoxides is introduced. The weakly acidic alpha protons of sulfoxides are reversibly deprotonated by LiOtBu, and an indole-based phosphine ligated palladium complex facilitates the arylation reactions. A variety of (hetero)aryl methyl sulfoxides were successfully cross coupled with aryl bromides. More challenging coupling partners, such as alkyl methyl sulfoxides (including DMSO) proved to be suitable under the optimized conditions. Moreover, aryl chlorides were employed as electrophiles in our protocol by using Buchwald-type precatalyst. This method was utilized to synthesize bioactive benzyl sulfoxide intermediates.
520
$a
In chapter 2, we presented a novel approach to produce diaryl sulfoxides from aryl benzyl sulfoxides. Optimization of the reaction conditions was led by High-Throughput Experimentation (HTE) techniques. A single Pd(dba)2/NiXantPhos based catalyst successfully promotes a triple relay process involving sulfoxide alpha-arylation, C-S bond-cleavage, and C-S bond-formation. Byproduct benzophenone is formed by an additional palladium-catalyzed process. It is noteworthy that palladium catalyzed benzylative substitution to cleavage C-S bond of sulfoxides is unprecedented. A wide range of (hetero)aryl benzyl sulfoxides, as well as alkyl benzyl sulfoxides with various (hetero)aryl bromides were employed in the triple relay process in good to excellent yields (85-99%). Moreover, aryl methyl sulfoxides, dibenzyl sulfoxides and DMSO could be utilized to generate diaryl sulfoxides involving multiple catalytic cycles by a single catalyst.
520
$a
In chapter 3, we investigated diaryl sulfoxides generation from aryl benzyl sulfoxides and aryl chlorides via three sequential catalytic cycles all promoted by a NiXantPhos-based palladium catalyst. The key step is S-arylation of a sulfenate anion. An air- and moisture-stable palladacyclic precursor derived from NiXantPhos efficiently facilitated the transformation. Various functional groups, especially those with acidic protons, were tolerated. This method can also be extended to methyl and dibenzyl sulfoxides substrates.
590
$a
School code: 0175.
650
4
$a
Analytical chemistry.
$3
3168300
650
4
$a
Organic chemistry.
$3
523952
690
$a
0486
690
$a
0490
710
2
$a
University of Pennsylvania.
$b
Chemistry.
$3
2096482
773
0
$t
Dissertation Abstracts International
$g
76-11B(E).
790
$a
0175
791
$a
Ph.D.
792
$a
2015
793
$a
English
856
4 0
$u
http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3709485
筆 0 讀者評論
館藏地:
全部
電子資源
出版年:
卷號:
館藏
1 筆 • 頁數 1 •
1
條碼號
典藏地名稱
館藏流通類別
資料類型
索書號
使用類型
借閱狀態
預約狀態
備註欄
附件
W9300566
電子資源
11.線上閱覽_V
電子書
EB
一般使用(Normal)
在架
0
1 筆 • 頁數 1 •
1
多媒體
評論
新增評論
分享你的心得
Export
取書館
處理中
...
變更密碼
登入