Sonogashira coupling in 3D-printed NMR cuvettes: synthesis and properties of arylnaphthylalkynes

被引：21

作者：

Lederle, Felix ^{[1
]}

Meyer, Frederick ^{[1
]}

Kaldun, Christian ^{[1
]}

Namyslo, Jan C. ^{[1
]}

Huebner, Eike G. ^{[1
]}

机构：

[1] Tech Univ Clausthal, Inst Organ Chem, Leibnizstr 6, D-38678 Clausthal Zellerfeld, Germany

来源：

NEW JOURNAL OF CHEMISTRY | 2017年 / 41卷 / 05期

关键词：

NONLINEAR-OPTICAL-PROPERTIES; STATE DIPOLE-MOMENTS; ONE-POT SYNTHESIS; COPPER-FREE; CHEMICAL-SYNTHESIS; SOLVATOCHROMIC METHOD; ORGANIC-MOLECULES; ARYL BROMIDES; TRIPLE BOND; REACTIONWARE;

D O I：

10.1039/c6nj03614g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

3D-Printing has been used to build hollow NMR tube/spinner combinations out of NMR-transparent polyamide. The whole 3D-print has been processed inside a glove box and during pauses of the 3D-printing process, all reactants for the palladium-catalyzed decarboxylative Sonogashira coupling of aryl halides with arylpropiolic acids have been inserted. Within the totally gas tight and pressure resistant tubes, a set of arylnaphthylalkynes has been synthesized and the progress of the reaction has been monitored via NMR spectroscopy. The (nonlinear) optical properties of the push-pull substituted bis(aryl)alkynes have been investigated by fluorescence spectroscopy and DFT calculations. A significant correlation between the intensity of the triple-bond stretching vibration and the calculated first hyperpolarizability is reported.

引用

页码：1925 / 1932

页数：8

共 71 条

[51] Decarboxylative coupling reactions: a modern strategy for C-C-bond formation
Rodriguez, Nuria
Goossen, Lukas J.
[J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 5030 - 5048
[52] Can polarization of triple bond in tolanes be deduced from 13C NMR shifts? : Re-evaluation of factors affecting regiochemistry of the palladium-catalyzed hydrostannation of alkynes
Rubin, M
Trofimov, A
Gevorgyan, V
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (29) : 10243 - 10249
[53] A Guide to Sonogashira Cross-Coupling Reactions: The Influence of Substituents in Aryl Bromides, Acetylenes, and Phosphines
Schilz, Marc
Plenio, Herbert
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (06) : 2798 - 2807
[54] Estimation of the ground and the first excited singlet-state dipole moments of 1,4-disubstituted anthraquinone dyes by the solvatochromic method
Siddlingeshwar, B.
Hanagodimath, S. M.
[J]. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2010, 75 (04) : 1203 - 1210
[55] Siemsen P, 2000, ANGEW CHEM INT EDIT, V39, P2633
[56] Effect of counterions on the interactions of charged oligothiophenes
Singh-Miller, Nicholas E.
Scherlis, Damian A.
Marzari, Nicola
[J]. JOURNAL OF PHYSICAL CHEMISTRY B, 2006, 110 (49) : 24822 - 24826
[57] Aryl/hetero-arylethyne bridged dyes: the effect of planar π-bridge on the performance of dye-sensitized solar cells
Song, Jun-Ling
Amaladass, Pitchamuthu
Wen, Shu-Hao
Pasunooti, Kalyan Kumar
Li, An
Yu, Yao-Lun
Wang, Xin
Deng, Wei-Qiao
Liu, Xue-Wei
[J]. NEW JOURNAL OF CHEMISTRY, 2011, 35 (01) : 127 - 136
[58] Development of Pd-Cu catalyzed cross-coupling of terminal acetylenes with sp2-carbon halides
Sonogashira, K
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 653 (1-2) : 46 - 49
[59] CONVENIENT SYNTHESIS OF ACETYLENES - CATALYTIC SUBSTITUTIONS OF ACETYLENIC HYDROGEN WITH BROMOALKENES, IODOARENES, AND BROMOPYRIDINES
SONOGASHIRA, K
TOHDA, Y
HAGIHARA, N
[J]. TETRAHEDRON LETTERS, 1975, (50) : 4467 - 4470
[60] A SERIES OF DONOR-ACCEPTOR MOLECULES OF THE FORM NH2(C6H4)(C=C)N(C6H4)NO2 - UNUSUAL EFFECTS OF VARYING-N
STIEGMAN, AE
MISKOWSKI, VM
PERRY, JW
COULTER, DR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) : 5884 - 5886

← 1 2 3 4 5 6 7 8 →