An Atom-Economic Route to Thiophenes and 2,2′-Bithiophenes by Intramolecular Transannulation of gem-Dialkylthio Enynes

被引：40

作者：

Fang, Guichun ^{[1
]}

Li, Jichun ^{[1
]}

Wang, Yeming ^{[3
]}

Gou, Mingyu ^{[1
]}

Liu, Qun ^{[1
]}

Li, Xingqi ^{[1
]}

Bi, Xihe ^{[1
,2
]}

机构：

[1] NE Normal Univ, Dept Chem, Changchun 130024, Peoples R China

[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

[3] Jilin Normal Univ, Dept Chem, Siping 136000, Peoples R China

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 16期

关键词：

ONE-POT SYNTHESIS; REDUCTIVE CYCLIZATION; VINYL SULFONES; FACILE; PYRROLES; FURANS; ANION; KETENE-S; S-ACETALS; VINYLALLENES; DERIVATIVES;

D O I：

10.1021/ol4017854

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An atom-economic route to thiophenes and bithiophenes has been developed starting from the readily available gem-dialkylthio enynes. A range of functionalized thiophenes and bithiophenes, bearing a pendent vinylthio group, were obtained in good to high yields under mild conditions.

引用

页码：4126 / 4129

页数：4

共 50 条

[1] An Extremely Facile Synthesis of Furans, Pyrroles, and Thiophenes by the Dehydrative Cyclization of Propargyl Alcohols
Aponick, Aaron
Li, Chuan-Ying
Malinge, Jeremy
Marques, Emerson Finco
[J]. ORGANIC LETTERS, 2009, 11 (20) : 4624 - 4627
[2] Biehl E. R., 2012, TOP HETEROCYCL CHEM, V29, P347
[3] AN ECONOMICAL AND CONVENIENT SYNTHESIS OF PHENYL VINYL SULFONE FROM BENZENETHIOL AND 1,2-DICHLOROETHANE
BRACE, NO
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) : 4506 - 4508
[4] Rhodium-catalyzed alkyne hydrothiolation with aromatic and aliphatic thiols
Cao, CS
Fraser, LR
Love, JA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (50) : 17614 - 17615
[5] A highly active catalyst for the reductive cyclization of ortho-nitrostyrenes under mild conditions
Davies, IW
Smitrovich, JH
Sidler, R
Qu, CX
Gresham, V
Bazaral, C
[J]. TETRAHEDRON, 2005, 61 (26) : 6425 - 6437
[6] Theoretical evidence for oxygenated intermediates in the reductive cyclization of nitrobenzenes
Davies, IW
Guner, VA
Houk, KN
[J]. ORGANIC LETTERS, 2004, 6 (05) : 743 - 746
[7] Diederich F, 2005, ACETYLENE CHEMISTRY: CHEMISTRY, BIOLOGY AND MATERIAL SCIENCE, pV
[8] gem-Dialkylthio vinylallenes: alkylthio-regulated reactivity and application in the divergent synthesis of pyrroles and thiophenes
Fang, Zhongxue
Yuan, Haiyan
Liu, Ying
Tong, Zixun
Li, Huiqin
Yang, Jin
Barry, Badru-Deen
Liu, Jianquan
Liao, Peiqiu
Zhang, Jingping
Liu, Qun
Bi, Xihe
[J]. CHEMICAL COMMUNICATIONS, 2012, 48 (70) : 8802 - 8804
[9] Fichou D., 1999, Handbook of Oligo- and Polythiophenes
[10] Gronowitz S., 2004, THIOPHENES

← 1 2 3 4 5 →