Arylboronates, hydroarylation with

A Pd-catalyzed reaaion of an arylboronic acid with aliphatic nitriles led to 2-arylbenzo[lr]furans (13S2241). A Pd-catalyzed addition of potassium aryltri-fluoroborates to ahphatic nitriles produced 2-arylbenzo[lr]furans (13JOC5273). A tandem chemoselective synthesis of 2-arylbenzo[lr]furans was accomplished from o-hydroxy- em-(dibromovinyl)benzenes and BiArj re nts under palladium-catalyzed conditions (12EJOC781). 2,3-Diarylnaphthofurans were generated using sequential hydroarylation of naphthols and alkynes in the presence of In(OTf)3 under microwave irradiation (13OL2190). 

Asymmetric hydroarylation of diphenylphosphinylallenes [Ph2P(0)]C(R)=C=CH2 with arylboronic acids ArB(OH)2, catalysed by an Rh-BINAP complex, has been shown to proceed in high yields with high regio- and enantio-selectivity to afford chiral allylphosphine oxides [Ph2P(0)]CH(R)C(Ar)=CH2 of up to 98% ee. A Tr-allylrhodium complex has been identified as the key intermediate.109... 

Hayashi. T.. Inoue. K.. Taniguchi, N., and Ogasawara, M., Rhodium-catalyzed hydroarylation of alkynes with arylboronic acids. 1,4-Shift of rhodium from 2-ai yl-l-alkcnylrhodium to 2-alkenylaryl-rhodium intermediate. 7. Am. Chem. Soc., 123, 9918, 2001. 

Asymmetric hydroarylation of styrenes and dienes RCH=CH2 with arylboronates ArB(OR)2, catalysed by (5 )-(Pr Box)PdCl2 (7.5 mol%) and Bu OK (5 mol%), can be attained under oxygen atmosphere to produce RCH(Ar)-Me with <75% ee. The competing -elimination is largely suppressed under these conditions. ... 

The rhodium-catalyzed asymmetric hydroarylation of diphenylphosphinylallenes with arylboronic acids furnished P,y-unsaturated diphenylphosphine oxides (Scheme 37). ... 

Scheme4.27 Rhodium-catalyzed hydroarylation of alkynes with arylboronic acids.

Lautens and Yoshida reported a similar rhodium-catalyzed hydroarylation of alkynes with arylboronic acids, where ortho nitrogen heteroaromatic alkynes were employed to favor a high regioselectivity [43]. The reaction of 2-(l-hexynyl)pyridine (67a) with 2-methylphenylboronic acid (2v) and [RhCl(cod)]2/69 catalyst in the presence of sodium carbonate and sodium dodecyl sulfate (SDS) in water gave a 84% yield of the addition product 68av with high regioselectivity (Scheme 4.31). Under these conditions, the addition of arylboronic acids was also observed for several other or-... 

Nishimura T, Hirabayashi S, Yasuhara Y, Hayashi T. Rhodium-catalyzed asymmetric hydroarylation of diphenyl-phosphinylaUenes with arylboronic acids. J. Am. Chem. Soc. 2006 128 2556 2557. 

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