A facile and less expensive monophosphinite ligand 2-(diphenylphosphinoxy)-naphthyl, C H OPPh (1) has been synthesized from the reaction 10 7 2 f -naphthol with chlorodiphenylphosphine. The mixture of Pd(OAc)2 and 1 catalyzes the Suzuki cross-coupling of a variety of aryl halides with ryl boronic acids at room temperature or at 60 ◦C, giving generally high yields even under low catalytic loads....

A dual visible light photoredox and gold-catalysed C(sp(2))-C(sp(2)) cross coupling is described. The success of this mild, oxidant- and base-free cross coupling is highly dependent on the amount of water added. Mechanistic studies show two distinct pathways depending on the gold catalyst employed: transmetallation of the arylboronic acid with gold(i) occurs prior to oxidation of gold(i) to gol...

A well-defined NHC-Pd(II)-Im complex 1 was found to be an effective catalyst for the Suzuki-Miyaura coupling of aryl sulfonates including tosylates and phenylsulfonates with arylboronic acids, giving the desired coupling products in good to high yields. Acceptable yields can also be achieved even by using the less reactive mesylates as the substrates. It is worthy of noting here that this is th...

Highly electrophilic aryl(2,2,2-trifluoroethyl)iodonium triflates have been used for the first time as trifluoroethyl and aryl transfer reagents in Pd-catalyzed functionalization of arylboronic acids. Electron-rich arylboronic acids reacted with aryl(2,2,2-trifluoroethyl)iodonium triflates (2a-b) in CH3CN in the presence of Pd2(dba)3 and K3PO4 at room temperature to provide trifluoroethyl arene...

The first enantioselective Pd-catalyzed construction of all-carbon quaternary stereocenters via 1,4addition of arylboronic acids to β-substituted cyclic enones is reported. Reaction of a wide range of arylboronic acids and cyclic enones using a catalyst prepared from Pd(OCOCF3)2 and a chiral pyridinooxazoline ligand yields enantioenriched products bearing benzylic stereocenters. Notably, this t...

Treatment of β-fluoroalkylated-α,β-unsaturated ketones with 1.2 equiv. of various arylboronic acids in the presence of 5 mol% of [Rh(COD)(2)]BF(4) and 6 mol% of (S)-BINAP in toluene/H(2)O (v/v = 4/1) at the reflux temperature for 3 h gave the corresponding Michael adducts in high yields with over 90% enantioselectivity. Though other electron-deficient alkenes, such as vinylsulfone and vinylphos...

Palladium(II)-catalyzed oxidative carbocyclizations represent an important class of reactions, which have provided powerful and atom-economical approaches to carboand heterocycles. In particular, oxidative carbocyclization strategies have been efficiently applied to total synthesis. As a continuation of our research on the palladium-catalyzed oxidative carbocyclizations of dienallenes and enall...

5-Aryl-2(5H)-furanones can be synthesized by the Rh-catalyzed reactions of arylboronic acids with internal alkynes under a CO atmosphere.

Transmetalation is a key elementary reaction of many important catalytic reactions. Among these, 1,4-addition of arylboronic acids to organic acceptors such as α,β-unsaturated ketones has emerged as one of the most important methods for asymmetric C-C bond formation. A key intermediate for the B-to-Rh transfer arising from quaternization on a boronic acid by a Rh-bound hydroxide (the active cat...