J.-M. Weibel, P. Pale et al.
rivative (1.2 equiv, 0.6 mmol) in degassed THF (3 mL, 6 mLmmolÀ1
)
[10] a) P. Y. Wong, W. K. Chow, K. H. Chung, C. M. So, C. P. Lau, F. Y.
c) P. Y. Choy, W. K. Chow, C. M. So, C. P. Lau, F. Y. Kwong, Chem.
[11] For selected examples, see: a) M. Lꢄthy, R. J. K. Taylor, Tetrahedron
L. S. Soebjerg, A. T. Lindhardt, K. L. Jensen, T. Skrydstrup, J. Org.
Chem. 2008, 73, 3404–3410; d) L. Zhang, T. Meng, J. Wu, J. Org.
[14] T. M. Gøgsig, J. Kleimark, S. O. Nilsson Lill, S. Korsager, A. T. Lind-
[15] Common current prices for 25 or 50 g batches (euro per mol,
ABCR (Germany)/Sigma–Aldrich, 2012) of Ts2O: 1540/2089; Tf2O:
667/1594; MsCl: –/25, TsCl: –/70, NsCl: 264/448.
[16] As bioactive motif, see: a) A. Lacy, R. OꢅKennedy, Curr. Pharm.
Des. 2004, 10, 3797–3811; b) I. Kostova, Curr. Med. Chem. Anti-
Cancer Agents 2005, 5, 29–46; c) F. Borges, F. Roleira, N. Milhazes,
L. Santana, E. Uriarte, Curr. Med. Chem. 2005, 12, 887–916; as fluo-
rescent marker in biology, see: d) D. Wahler, F. Badalassi, P. Crotti,
J. L. Reymond, Angew. Chem. 2001, 113, 4589–4592; Angew. Chem.
Int. Ed. 2001, 40, 4457–4460; as dyes for solar cell and laser applica-
tions, see: e) X. Liu, J. M. Cole, P. G. Waddell, T.-C. Lin, J. Radia,
A. Zeidler, J. Phys. Chem. A 2012, 116, 727–737; as polymer photo-
cross-linker, see: f) S. R. Trenor, A. R. Shultz, B. J. Love, T. E. Long,
Chem. Rev. 2004, 104, 3059–3077.
[18] G. M. Boland, D. M. X. Donnelly, J.-P. Finet, M. D. Rea, J. Chem.
under argon. After 5 min of stirring, the palladium catalyst (2 mol%)
and the alkenyl nosylate (1 equiv, 0.5 mmol) were successively added to
the reaction mixture. The mixture was kept at room temperature or
warmed to 308C and stirred until consumption of the starting material
(TLC). The reaction mixture was partitioned between Et2O (9 mL) and
water (9 mL) and the layers separated. The aqueous layer was extracted
with EtOAc (3ꢃ9 mL), and the combined organic layers were dried over
Na2SO4 and evaporated in vacuo. The crude residue was purified by flash
chromatography (cyclohexane/EtOAc gradient).
Acknowledgements
The authors thank the CNRS and the French Agency of Research (ANR
09-BLAN-0329 CADISCOM and ANR 11-JS07-001-01 SyntHetAu) for
financial support. N.P.C. also thanks the ANR for a PhD fellowship. A.D.
thanks the French Ministry of Research for a PhD fellowship.
Keywords: arenes
· cross-coupling · palladium · vinyl
compounds
[1] a) C. C. C. Johansson Seechurn, M. O. Kitching, T. J. Colacot, V.
Snieckus, Angew. Chem. 2012, 124, 5150–5174; Angew. Chem. Int.
Ed. 2012, 51, 5062–5085; b) J. Tsuji, Palladium Reagents and Cata-
lysts: New Perspectives for the 21st Century, Wiley, Hoboken, 2005;
c) Handbook of Organopalladium Chemistry for Organic Synthesis,
Vol. 1 (Ed.: E.-I. Negishi), Wiley, Hoboken, 2002, Part III; d) T. N.
Mitchell in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Die-
derich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 4.
[3] a) M. V. N. De Souza, Curr. Org. Synth. 2006, 3, 313–326; b) T. N.
[19] M. D. Santana, R. Garcia-Bueno, G. Garcia, G. Sanchez, G. Garcia,
A. R. Kapdi, M. Naik, S. Pednekar, J. Perez, L. Garcia, E. Perez,
340–348; b) for Hiyama coupling, see: Y. Nakao, T. Hiyama, Chem.
[5] a) A. B. Dounay, L. E. Overman in The Mizoroki-Heck Reaction
(Ed.: M. Oestreich), Wiley, Chichester, 2009, Chapter 16; b) I. P. Be-
[8] a) P. J. Stang, M. Hanack, L. R. Subramanian, Synthesis 1982, 85–
126; b) S. Chassaing, S. Specklin, J.-M. Weibel, P. Pale, Curr. Org.
Synth. 2012, 9, 806–827; c) S. Chassaing, S. Specklin, J.-M. Weibel, P.
Pale, Tetrahedron 2012, 68, 7245–7273.
[20] Halides or other additives are commonly added in Stille couplings.
They enhance the stannane nucleophilicity and, in the case of cati-
onic palladium intermediates, they coordinate to the stannane, ren-
dering the complex neutral, more stable, and thereby facilitating
transmetalation; see: P. Espinet, A. M. Echavarren, Angew. Chem.
2004, 116, 4808–4839; Angew. Chem. Int. Ed. 2004, 43, 4704–4734.
[22] a) S. Y. Yunusov, G. P. Sidyakin, Zh. Obshch. Khim. 1955, 25, 2009–
2016; b) J. Koyama, I. Toyokuni, K. Tagahara, Chem. Pharm. Bull.
1999, 47, 1038–1039.
[23] Poisoning of the catalyst by quinoline might account for this result.
Thus, we used a bulkier ligand and heating to minimize such phe-
nomenon.
Received: January 14, 2013
Published online: && &&, 0000
&
4
&
ꢂ 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Chem. Eur. J. 0000, 00, 0 – 0
ÝÝ
These are not the final page numbers!