Page 12 - From -Arylation of Olefins to Acylation with Aldehydes: A Journey in Regiocontrol of the Heck Reaction
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R-Arylation of Olefins to Acylation with Aldehydes Ruan and Xiao
Jianliang Xiao received his B.Eng. in chemical engineering at 10 Deeth, R. J.; Smith, A.; Brown, J. M. Electronic control of the regiochemistry in palladium-
Northwest University. This was followed by a M.Eng. in catalytic phosphinecatalyzedintermolecularHeckreactions.J.Am.Chem.Soc.2004,126,7144–7151.
engineering with Profs. Chi Wu and Junyu Wang at the Research 11 Henriksen, S. T.; Norrby, P.-O.; Kaukoranta, P.; Andersson, P. G. Combined experimental
and theoretical study of the mechanism and enantioselectivity of palladium-catalyzed
Institute of Petroleum Processing and a Ph.D. in chemistry with Prof. intermolecular Heck coupling. J. Am. Chem. Soc. 2008, 130, 10414–10421.
Marty Cowie at the University of Alberta. After a postdoctoral 12 (a) Bengston, A.; Larhed, M.; Hallberg, A. Protected indanones by a Heck-aldol annulation
appointment with Prof. Richard Puddephatt, he joined the ERATO reaction. J. Org. Chem. 2002, 67, 5854–5856. (b) Olofsson, K.; Larhed, M.; Hallberg, A.
Highly regioselective palladium-catalyzed internal arylation of allyltrimethylsilane with aryl
Molecular Catalysis Project directed by Prof. Noyori. In 1996 he triflates. J. Org. Chem. 1998, 63,5076–5079. (c) Larhed, M.; Hallberg, A. Direct synthesis
took up a Principal Scientist position at the University of Liverpool of cyclic ketals of acetophenones by palladium-catalyzed arylation of hydroxyalkyl vinyl
ethers. J. Org. Chem. 1997, 62,7858–7862. (d) Karabelas, K.; Westerlund, C.; Hallberg,
and was appointed to a Lectureship in the Chemistry Department A. The effect of added silver nitrate on the palladium-catalyzed arylation of allyltrimethyl-
in 1999; this was followed by promotion to full Professor in early silanes. J. Org. Chem. 1985, 50, 3896–3900.
2005. He was awarded the UK Prize for Process Chemistry 13 (a) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. 1,l0-Phenanthroline derivatives: a new
ligand class in the Heck reaction. Mechanistic aspects. J. Org. Chem. 1993, 58, 7421–
Research 2008.
7426. (b) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. Palladium-catalyzed arylation of
unsymmetrical olefins. Bidentatephosphine ligand controlled regioselectivity. J. Org. Chem.
We are indebted to all our co-workers and collaborators and in 1992,57,3558–3563. (c) Cabri,W.;Candiani,I.;Bedeschi, A.;Santi, R. Ligand-controlled
R-regioselectivity in palladium-catalyzed arylation of butyl vinyl ether. J. Org. Chem. 1990,
particular to those involved in this study for their invaluable 55,3654–3655.
14 Xu, L.; Chen, W.; Ross, J.; Xiao, J. Palladium-catalyzed regioselective arylation of an
intellectual and experimental contributions. Their names are seen
electron-rich olefin by aryl halides in ionic liquids. Org. Lett. 2001, 3, 295–297.
in the references cited. We also acknowledge the EPSRC (EP/ 15 Mo, J.; Xu,L.; Xiao, J.Ionicliquid-promoted, highlyregioselectiveHeckarylationof electron-
rich olefins by aryl halides. J. Am. Chem. Soc. 2005, 127,751–760.
F000316 and EP/C005643), Pfizer, AstraZeneca, NPIL Pharma
16 Pei, W.; Mo, J.; Xiao, J. Highly regioselective Heck reactions of heteroaryl halides with
UK, Johnson Matthey, and the University of Liverpool for electron-rich olefins in ionic liquid. J. Organomet. Chem. 2005, 690, 3546–3551.
financial support. 17 Hyder, Z.;Mo,J.;Xiao, J.Palladium-catalyseddirect regioselectivesynthesisof cyclic ketals
from electron-rich olefins and aryl bromides in ionic liquids. Adv. Synth. Catal. 2006, 348,
1699–1704.
FOOTNOTES 18 Mo, J.; Liu, S.; Xiao, J. Palladium-catalyzed regioselective Heck arylation of electron-rich
olefins in a molecular solvent-ionic liquid cocktail. Tetrahedron 2005, 61, 9902–9907.
*To whom correspondence should be addressed. Telephone: (44)-151-7942937. Fax:
(44)-151-7943588. E-mail: j.xiao@liv.ac.uk. 19 Mo, J.; Xu, L.; Ruan, J.; Liu, S.; Xiao, J. Regioselective Heck arylation of unsaturated
alcohols by palladium catalysis in ionic liquid. Chem. Commun. 2006, 3591–3593.
20 Chalk, A. J.; Magennis, S. A. Palladium-catalyzed vinyl substitution reactions. I. New
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