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2,5-Bis-(butyltelluro) Thiophene As A Convenient Precursor For The Synthesis Of 2,5-bis-(acetylenic) Thiophenes

G. Zeni, C. Nogueira, Dagoberto O. Silva, P. Menezes, A. Braga, H. Stefani, J. B. Rocha
Published 2003 · Chemistry

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Both symmetrically and unsymmetrically substituted 2,5-bis-(acetylenic) thiophene derivatives were obtained in good yields under mild conditions through palladium-catalyzed cross coupling reaction of 2,5-bis-(butyltelluro) thiophene 2 and terminal alkynes. The methodology represents a general and efficient protocol for carrying out the synthesis of thiophene derivatives with potential biological activities.
This paper references
10.1016/S0040-4039(98)02352-1
Highly unsaturated conjugated systems from vinylic tellurides
R. Barrientos-Astigarraga (1999)
10.1002/9783527615278
Modern acetylene chemistry
P. Stang (1995)
10.1016/0045-6535(89)90080-5
PHOTOACTIVE ANTIVIRAL AND CYTOTOXIC ACTIVITIES OF SYNTHETIC THIOPHENES AND THEIR ACETYLENIC DERIVATIVES
J. Hudson (1989)
10.1055/S-1980-29145
A Convenient Synthesis of Ethynylarenes and Diethynylarenes
S. Takahashi (1980)
10.1055/S-2006-957872
Antibacterial and antifungal polyine compounds from Glehnia littoralis ssp. leiocarpa.
H. Matsuura (1996)
10.1016/S0022-328X(00)00828-7
Carbon–carbon bond formation by means of organotellurium compounds
R. Barrientos-Astigarraga (2001)
10.1055/S-2001-16799
Stereoselective Synthesis of (Z)-Enynes via Pd(II)/CuI(I)-Catalyzed Cross-Coupling Reaction of bis-Vinylic Tellurides with 1-Alkynes
G. Zeni (2001)
10.1055/S-1995-5223
Stereoselective and Convergent Route to Z-Enynes and Z-Trisubstituted Enediynes
M. A. D. Araujo (1995)
10.1016/S0040-4039(00)72170-8
Synthese d'enynes et de dienes conjugues a l'aide d'organocuivreux vinyliques. application a la synthese du bombykol.
J. Normant (1975)
10.1016/S0022-328X(00)00909-8
Weakly ligated palladium complexes PdCl2(RCN)2 in piperidine: versatile catalysts for Sonogashira reaction of vinyl chlorides at room temperature
M. Alami (2001)
10.1021/jo00213a021
Palladium-catalyzed olefination of vinyl triflates
W. Scott (1985)
10.1002/ANIE.199113873
Chemistry and Biology of the Enediyne Anticancer Antibiotics
K. C. Nicolaou (1991)
10.1016/0040-4020(96)00016-6
The Chemistry of Enediynes, Enyne Allenes and Related Compounds
J. Grissom (1996)
10.1039/P19770000887
High-yield syntheses of dilithio-derivatives of furan, thiophen, N-methylpyrrole, 3-methylfuran, and 3-methylthiophen. Application of the method to 2-methylfuran, 2-methylthiophen, 2,5-dimethylfuran, 2,5-dimethylthiophen, benzo[b]furan, benzo[b]thiophen, pyrrole, and indole
D. J. Chadwick (1977)
10.1016/S0040-4039(99)00773-X
Coupling of Z-vinylic tellurides with alkynes catalysed by : synthesis of Z-enynes and Z-enediynes
G. Zeni (1999)
10.1016/0048-3575(87)90078-2
Toxicokinetics of the phototoxic allelochemical α-terthienyl in three herbivorous lepidoptera
S. Iyengar (1987)
10.1055/S-1979-28851
Vinyl-Copper Derivatives; X1. Alkylation of (Z)-Dialkenylcuprates
A. Alexakis (1979)
10.1055/S-2000-7594
1,2-Dihalogenalkenes: Useful Linchpins to Unsaturated Compounds via Palladium or Nickel Catalysis
M. Alami (2000)
10.1016/S0040-4039(00)91094-3
A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines
K. Sonogashira (1975)
10.1021/JA00475A059
Selective carbon-carbon bond formation via transition metal catalysts. 9. Double metal catalysis in the cross-coupling reaction and its application to the stereo- and regioselective synthesis of trisubstituted olefins
E. Negishi (1978)
10.1016/S0040-4020(01)00764-5
Regioselective palladium-catalyzed cross-coupling reactions in the synthesis of novel 2,3-disubstituted thiophene derivatives
R. Pereira (2001)
10.1016/S0040-4039(01)01703-8
Synthesis and anti-inflammatory activity of acetylenic thiophenes
G. Zeni (2001)
10.1016/0040-4039(91)80759-Y
A novel approach to the synthesis of enediynes
P. A. Magriotis (1991)
10.1016/S0031-9422(00)91121-X
Ultraviolet-mediated antibiotic activity of thiophene compounds of Tagetes
G. Chan (1975)
10.1021/JA00290A037
Novel and convenient method for the stereo- and regiospecific synthesis of conjugated alkadienes and alkenynes via the palladium-catalyzed cross-coupling reaction of 1-alkenylboranes with bromoalkenes and bromoalkynes
N. Miyaura (1985)
10.1016/S0040-4039(01)85081-4
An efficient stereospecific synthesis of olefins by the palladium-catalyzed reaction of grignard reagents with alkenyl iodides.
Huu Phuong Dang (1978)
10.1016/0040-4039(91)80765-X
An efficient palladium-catalyzed reaction of vinyl chlorides with terminal acetylenes
M. Alami (1991)
10.1016/S0022-328X(00)94049-X
Palladium catalyzed synthesis of aryl, heterocyclic and vinylic acetylene derivatives
H. A. Dieck (1975)



This paper is referenced by
10.1016/B0-08-044655-8/00021-0
1.21 – Alkynes
E. Tyrrell (2005)
10.1002/EJOC.200700599
Palladium‐Catalyzed Carbonylation of 2‐Haloselenophenes: Synthesis of Selenophene‐2‐carboxamides, Selenophene‐2,5‐dicarboxamides and N,N′‐Bridged Selenophene‐2‐carboxamides
P. Prediger (2007)
10.1002/CHIN.200318096
2,5‐Bis‐(butyltelluro) Thiophene as a Convenient Precursor for the Synthesis of 2,5‐Bis‐(acetylenic) Thiophenes.
G. Zeni (2003)
10.1016/B0-08-045047-4/00121-7
9.13 – Tellurium
J. V. Comasseto (2007)
10.1016/J.TET.2006.07.097
Introduction of ethynylene and thienylene spacers into 2,5-diarylthiazole and 2,5-diarylthiophene
K. Kobayashi (2006)
10.1039/b401059k
Stereoselective preparation of conjugated E-enynes from E-vinylic tellurides and terminal alkynes via Sonogashira cross-coupling.
G. Zeni (2004)
10.1016/S0959-6380(05)80047-9
Chapter 5.1 Five-membered ring systems: Thiophenes & Se, Te analogs
Venkataramanan Seshadri (2005)
10.1016/J.CCR.2005.03.033
Transition metals in organic synthesis: Highlights for the year 2003
B. Soederberg (2006)
10.1016/J.LFS.2004.10.038
Antinociceptive properties of acetylenic thiophene and furan derivatives: evidence for the mechanism of action.
C. E. Goncales (2005)
10.1016/J.TETLET.2006.01.118
Palladium-catalyzed cross-coupling of 2-haloselenophene with terminal alkynes in the absence of additive
O. Barros (2006)
10.1007/s10989-010-9216-x
Solid-Phase Synthesis and NMR Structural Studies of the Marine Antibacterial Cyclic Tetrapeptide: Cyclo[GSPE]
H. A. Lim (2010)
10.1515/acph-2016-0005
Synthesis and structure elucidation of some novel thiophene and benzothiophene derivatives as cytotoxic agents
R. Mohareb (2016)
10.1071/CH08255
Synthesis of 2-Aryl- and 2,5-Diarylfurans and Thiophenes by Suzuki-Miyaura Reactions Using Potassium Trifluoroborate Salts and Heteroaryltellurides
Giancarlo V. Botteselle (2008)
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