Synthesis of S-acetyl oligoarylenedithiols via Suzuki-Miyaura cross-coupling

被引:31
作者
Operamolla, Alessandra [1 ]
Hassan Omar, Omar [2 ]
Babudri, Francesco [1 ,2 ]
Farinola, Gianluca M. [1 ]
Naso, Francesco [1 ,2 ]
机构
[1] Univ Bari, Dipartimento Chim, Via Orabona 4, I-70126 Bari, Italy
[2] CNR, ICCOM, Dipartimento Chim, I-70126 Bari, Italy
关键词
D O I
10.1021/jo701918z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Oligoarylenes with three or four aromatic rings, bearing two S-acetylated mercaptomethyl groups in 1,3 position on one end of the polyaromatic system and presenting various functionalities on the other terminal ring, have been synthesized by the Suzuki-Miyaura cross-coupling reaction. The use of palladium complexes with a Buchwald's phosphine as ligand allowed us to perform this coupling reaction also in the presence of benzylic S-acetyl-protected functionalities on the aromatic halide. The obtained oligoarylenes are potential novel candidates for the generation of self-assembling monolayers on metal substrates.
引用
收藏
页码:10272 / 10275
页数:4
相关论文
共 30 条
[1]   Synthesis of conjugated oligomers and polymers: the organometallic way [J].
Babudri, F ;
Farinola, GM ;
Naso, F .
JOURNAL OF MATERIALS CHEMISTRY, 2004, 14 (01) :11-34
[2]   Fluorinated organic materials for electronic and optoelectronic applications: the role of the fluorine atom [J].
Babudri, Francesco ;
Farinola, Gianluca M. ;
Naso, Francesco ;
Ragni, Roberta .
CHEMICAL COMMUNICATIONS, 2007, (10) :1003-1022
[3]   Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].
Barder, TE ;
Walker, SD ;
Martinelli, JR ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696
[4]   A novel Suzuki-type cross-coupling reaction of cyclopropylboronic esters with benzyl bromides [J].
Chen, H ;
Deng, MZ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (10) :1609-1613
[5]   Effect of functional group (fluorine) of aromatic thiols on electron transfer at the molecule-metal interface [J].
Chen, W ;
Wang, L ;
Huang, C ;
Lin, TT ;
Gao, XY ;
Loh, KP ;
Chen, ZK ;
Wee, ATS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (03) :935-939
[6]   Synthesis and characterization of conjugated mono- and dithiol oligomers and characterization of their self-assembled monolayers [J].
de Boer, B ;
Meng, H ;
Perepichka, DF ;
Zheng, J ;
Frank, MM ;
Chabal, YJ ;
Bao, ZN .
LANGMUIR, 2003, 19 (10) :4272-4284
[7]   Self-assembled monolayers based on chelating aromatic dithiols on gold [J].
Garg, N ;
Lee, TR .
LANGMUIR, 1998, 14 (14) :3815-3819
[8]   THIOPHENOL PROTECTING GROUPS FOR THE PALLADIUM-CATALYZED HECK REACTION - EFFICIENT SYNTHESES OF CONJUGATED ARYLTHIOLS [J].
HSUNG, RP ;
BABCOCK, JR ;
CHIDSEY, CED ;
SITA, LR .
TETRAHEDRON LETTERS, 1995, 36 (26) :4525-4528
[9]   Annealing effect of self-assembled monolayers generated from terphenyl derivatized thiols on Au(111) [J].
Ishida, T ;
Fukushima, H ;
Mizutani, W ;
Miyashita, S ;
Ogiso, H ;
Ozaki, K ;
Tokumoto, H .
LANGMUIR, 2002, 18 (01) :83-92
[10]   Practical thiol surrogates and protective groups for arylthiols for Suzuki-Miyaura conditions [J].
Itoh, T ;
Mase, T .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05) :2203-2206