Page 13 - From -Arylation of Olefins to Acylation with Aldehydes: A Journey in Regiocontrol of the Heck Reaction

R-Arylation of Olefins to Acylation with Aldehydes Ruan and Xiao

34 Liu, M.; Hyder, Z.; Sun, Y.; Tang, W.; Xu, L.; Xiao, J. Efficient synthesis of alkyl aryl ketones 38 Arvela, R. K.; Pasquini, S.; Larhed, M. Highly regioselective internal Heck arylation of
& ketals via palladium-catalyzed regioselective arylation of vinyl ethers. Org. Biomol. Chem. hydroxyalkyl vinyl ethers by aryl halides in water. J. Org. Chem. 2007, 72, 6390–6396.
2010, 8, 2012–2015. 39 Senn, H. M.; Ziegler, T. Oxidative addition of aryl halides to palladium(0) complexes: A
35 Xu, D.; Liu, Z.; Tang, W.; Xu, L.; Hyder, Z.; Xiao, J. Palladium-catalyzed regiocontrolled density-functional study including solvation. Organometallics 2004, 23, 2980–2988.
internal heteroarylation of electron-rich olefins with heteroaryl halides. Tetrahedron Lett. 40 Ruan,J.; Iggo,J.A.; Berry,N.G.; Xiao,J.Hydrogen-bonding-promotedoxidative addition
2008, 49, 6104–6107. and regioselective arylation of olefins with aryl chlorides. J. Am. Chem. Soc. 2010, 132,
36 McConville, M.; Blacker, J.; Xiao, J. Heck reaction in diols and cascade formation of cyclic 16689–16699.
ketals. Synthesis 2010, 49, 349–360. 41 Ruan, J.; Iggo, J. A.; Xiao, J. Direct synthesis of 1-indanones via Pd-catalyzed olefination
37 (a) Littke, A. F.; Fu, G. C. Versatile catalyst for Heck reactions of aryl chlorides and aryl and ethylene glycol-promoted aldol-type annulation cascade. Org. Lett. 2011, 13, 268–
bromidesundermild conditions.J.Am.Chem.Soc.2001,123, 6989–7000. (b)Schnyder, 271.
A.; Aemmer, T.; Indolese, A. F.; Pittelkow, U.; Studer, M. First application of secondary 42 Ruan, J.; Saidi, O.; Iggo, J. A.; Xiao, J. Direct acylation of aryl bromides with aldehydes by
phosphines as supporting ligands for the palladium-catalyzed Heck reaction: Efficient palladium catalysis. J. Am. Chem. Soc. 2008, 130, 10510–10511.
activation of aryl chlorides. Adv. Synth. Catal. 2002, 344, 495–498. (c) Datta, G. K.;
von Schenck, H.; Hallberg, A.; Larhed, M. Selective terminal Heck arylation of vinyl ethers 43 Colbon, P.; Ruan, J.; Purdie, M.; Xiao, J. Direct acylation of aryl chlorides with aldehydes by
with aryl chlorides: A combined experimental-computational approach including synthesis palladium-pyrrolidine co-catalysis. Org. Lett. 2010, 12,3670–3673.
of Betaxolol. J. Org. Chem. 2006, 71, 3896–3903. (d) Cal o, V.; Nacci, A.; Monopoli, A.; 44 This reaction can also be effected by using aryl boronic acid in acetone: Ruan, J.; Li, X.;
Cotugno, P. Heck reactions with palladium nanoparticles in ionic liquids: Coupling of aryl Saidi, O.; Xiao, J. Oxygen and base-free oxidative Heck reactions of arylboronic acids with
chlorides with deactivated olefins. Angew. Chem., Int. Ed. 2009, 48, 6101–6103. olefins. J. Am. Chem. Soc. 2008, 130, 2424–2425.

626 ’ ACCOUNTS OF CHEMICAL RESEARCH ’ 614–626 ’ 2011 ’ Vol. 44, No. 8