A novel stereoselective synthesis of (1Z,3E)-2-phenyl(or p-tolyl)sulfonyl-substituted 1,3-dienes via palladium catalyzed cross-coupling reactions of (E)-α-lodovinyl sulfones

被引：1

作者：

Hu Rong-Hua ^{[1
,2
]}

Chen Gui-Qin ^{[1
]}

Cai Ming-Zhong ^{[1
]}

机构：

[1] Jiangxi Normal Univ, Dept Chem, Nanchang 330027, Jiangxi, Peoples R China

[2] Jinggangshan Univ, Dept Chem, Jian 343009, Jiangxi, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2007年 / 25卷 / 12期

关键词：

(E)-alpha-iodovinyl sulfone; hydrozirconation; 1,3-dien-2-yl sulfone; palladium; cross-coupling;

D O I：

10.1002/cjoc.200790355

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(E)-alpha-Stannylvinyl phenyl(or p-tolyl)sulfones underwent an iododestannylation reaction to afford (E)-alpha-iodovinyl phenyl(or p-tolyl)sulfones 1, which reacted with (E)-alkenylzirconium(IV) complexes 2 produced in situ by hydrozirconation of terminal alkynes in the presence of a Pd(PPh3)(4) catalyst to afford stereoselectively (1Z,3E)-2phenyl(or p-tolyl)sulfonyl- substituted 1,3-dienes 3 in good yields.

引用

页码：1927 / 1931

页数：5

共 50 条

[31] Nickel-catalyzed cross-coupling of dienyl phosphates with Grignard reagents in the synthesis of 2-substituted 1,3-dienes
Sofia, A
Karlström, E
Itami, K
Bäckvall, JE
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05): : 1745 - 1749
[32] Nickel-catalyzed cross-coupling of dienyl phosphates with Grignard reagents in the synthesis of 2-substituted 1,3-dienes
Karlstrom, A. Sofia E.
Itami, Kenichiro
Backvall, Jan-E
Journal of Organic Chemistry, 1999, 64 (2-5): : 1745 - 1749
[33] Stereoselective synthesis of (E)-1,3-enynyl bromides via Pd/Cu-catalyzed cross-coupling reaction of (Z)-α-bromovinylstannanes
Cai, MZ
Zhao, H
CHINESE CHEMICAL LETTERS, 2004, 15 (10) : 1157 - 1160
[34] Stereoselective Synthesis of 1,3-Enynylstannanes via Palla-dium Catalyzed Cross-Coupling Reactions of (Z)-α-Bromovinylstannanes
蔡明中
章荣立
赵红
ChineseJournalofChemistry, 2004, (12) : 1417 - 1420
[35] Stereoselective synthesis of functionalized (1E,5E)-1,5-dien-3-ynes containing ester or sulfonyl groups by palladium-catalyzed addition and cross-coupling reactions
Hao, Wenyan
Xie, Shiyun
Wu, Yichao
Cai, Mingzhong
NEW JOURNAL OF CHEMISTRY, 2014, 38 (06) : 2686 - 2692
[36] A facile stereospecific synthesis of (Z)-2-sulfonyl-substituted 1,3-enynes via Sonogashira coupling of (E)-α-iodovinyl sulfones with 1-alkynes
Wen Yan Hao
ChineseChemicalLetters, 2007, (07) : 773 - 776
[37] A facile stereospecific synthesis of (Z)-2-sulfonyl-substituted 1,3-enynes via Sonogashira coupling of (E)-α-iodovinyl sulfones with 1-alkynes
Hao, Wen Yan
Jiang, Jian Wen
Cai, Ming Zhong
CHINESE CHEMICAL LETTERS, 2007, 18 (07) : 773 - 776
[38] Highly regioselective and stereoselective hydrostannylation of (Z)-2-ethoxycarbonyl-1,3-enynes leading to (1E,3E)-2-ethoxycarbonyl-3-stannyl-1,3-dienes
Wang, Pingping
Huang, Bin
Xie, Shiyun
Tuo, Yuxin
Cai, Mingzhong
JOURNAL OF CHEMICAL RESEARCH, 2015, (11) : 627 - 630
[39] The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates: an efficient synthesis of (1Z, 3E)-1-bromo/chloro-2-carboxy-1,3-dienes
Wang, Yanzhao
Lu, Biao
Zhang, Liming
CHEMICAL COMMUNICATIONS, 2010, 46 (48) : 9179 - 9181
[40] Stereospecific preparation of symmetrical (1Z, 3Z)- and (1E, 3E)-2,3-difluoro-1,4-disubstituted-buta-1,3-dienes from 1-bromo-1-fluoroalkenes
Xu, Jianjun
Burton, Donald J.
JOURNAL OF FLUORINE CHEMISTRY, 2007, 128 (01) : 71 - 77

← 1 2 3 4 5 →