Sulfur Heterocyclization and 1,3-Migration of Silicon in Reaction of 1,3-Diynes with Sodium Triisopropylsilanethiolate: One-Pot Synthesis of 2,5-Disubstituted 3-(Triisopropylsilyl)thiophenes

被引：7

作者：

Tang, Jialiang ^{[1
]}

Ming, Ling ^{[1
]}

Zhao, Xiaoming ^{[1
]}

机构：

[1] Tongji Univ, Dept Chem, State Key Lab Pollut Control & Resource Reuse, Shanghai 200092, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2013年 / 45卷 / 12期

关键词：

1,3-diynes; cyclizations; 1,3-migration of silicon; thiophene; sulfur heterocycles; TERMINAL ALKYNES; OPTICAL-PROPERTIES; THIOPHENES; GOLD; HYDROAMINATION; COMPLEXES; DESILYLATION; ALLENES; DONOR; CUCL;

D O I：

10.1055/s-0033-1338472

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sulfur heterocyclization and 1,3-migration of silicon have been realized in the reactions of a range of 1,3-diynes with sodium triisopropylsilanethiolate in N,N-dimethylformamide. These provided 40-72% yields of 2,5-disubstituted 3-(triisopropylsilyl)thiophenes and up to 50% yield of 2,5-disubstituted thiophenes.

引用

页码：1713 / 1718

页数：6

共 29 条

[1] Synthesis of 2,5-disubstituted thiophenes via metal-free sulfur heterocyclization of 1,3-diynes with sodium hydrosulfide [J].

Tang, Jialiang ;

Zhao, Xiaoming .

RSC ADVANCES, 2012, 2 (13) :5488-5490

[2] Copper(I)-Catalyzed Synthesis of 2,5-Disubstituted Furans and Thiophenes from Haloalkynes or 1,3-Diynes [J].

Jiang, Huanfeng ;

Zeng, Wei ;

Li, Yibiao ;

Wu, Wanqing ;

Huang, Liangbing ;

Fu, Wei .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (11) :5179-5183

[3] Direct One-Pot Construction of Diaryl Thioethers and 1,3-Diynes through a Copper(I)-Catalyzed Reaction of λ3-Iodanes with Thiophenols [J].

Li, Jun ;

Zhou, Chuang ;

Liang, Hong ;

Guo, Xiao-Qiang ;

Chen, Lian-Mei ;

Kang, Tai-Ran .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (30)

[4] New protocol for one-pot synthesis of functionalized symmetrical 1,4-dialkyl- or 1,4-diaryl-1,3-diynes [J].

Rzonsowska, Monika ;

Dudziec, Beata ;

Kownacki, Ireneusz ;

Marciniec, Bogdan .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2015, 775 :20-26

[5] One-pot synthesis of 1,4-diarylsubstituted 1,3-diynes from the sequential coupling reactions of aryl iodides and propiolic acid [J].

Kim, Yong ;

Park, Ahbyeol ;

Park, Kyungho ;

Lee, Sunwoo .

TETRAHEDRON LETTERS, 2011, 52 (15) :1766-1769

[6] Reduced graphene oxide supported copper oxide nanocomposites: An efficient heterogeneous and reusable catalyst for the synthesis of ynones, 1,3-diynes and 1,5-benzodiazepines in one-pot under sustainable reaction conditions [J].

Sarkar, Rajib ;

Gupta, Ajay ;

Jamatia, Ramen ;

Pal, Amarta Kumar .

APPLIED ORGANOMETALLIC CHEMISTRY, 2020, 34 (07)

[7] One-pot Synthesis of Alkynylated Coumarins via Rhodium-Catalyzed Annulation of Aryl Thiocarbamates with 1,3-Diynes or Terminal Alkynes [J].

Gao, Yuan ;

Zeng, Fenfen ;

Sun, Xudong ;

Zeng, Minfeng ;

Yang, Zhen ;

Huang, Xianqiang ;

Shen, Guodong ;

Tan, Yongsheng ;

Feng, Ruokun ;

Qi, Chenze .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (07) :1328-1333

[8] Ruthenium-Catalyzed trans-Hydrogermylation of Alkynes: Formation of 2,5-Disubstituted Germoles through Double trans-Hydrogermylation of 1,3-Diynes [J].

Matsuda, Takanori ;

Kadowaki, Sho ;

Yamaguchi, Yoshiyuki ;

Murakami, Masahiro .

ORGANIC LETTERS, 2010, 12 (05) :1056-1058

[9] Transition-Metal-Free Heterocyclization of 1,3-Diynes with Nitriles in the Presence of Aqueous Potassium Hydroxide: Synthesis of 2,4-Disubstituted 5-[(E)-2-Phenylethenyl]-1,3-oxazoles [J].

Ming, Ling ;

Tang, Jialiang ;

Zhao, Xiaoming .

SYNTHESIS-STUTTGART, 2014, 46 (18) :2499-2505

[10] Mg3N2-assisted one-pot synthesis of 1,3-disubstituted imidazo[1,5-a]pyridine [J].

Patil, Suhas G. ;

Jadhav, Jagannath S. ;

Sankpal, Sagar T. .

RSC ADVANCES, 2020, 10 (20) :11808-11815

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