An orthogonal set of Cu-catalysts for the selective mono-arylation of alkyl aryl diols using aryl iodides is presented. Picolinic acid ligated copper catalyst provided phenol O-arylation only, while alkyl aryl ethers are generated by ligand-free copper catalyst in the presence of 2 equivalents NaOt-Bu.

Cu-catalyzed cross-coupling of unactivated secondary alkyl iodides with alkyl Grignard reagents in the presence of 1,3-butadiene as a ligand precursor was developed. The use of 1,3-butadiene resulted in improved yields of alkyl-alkyl products with improved selectivities.

Herein we report a Pd-catalyzed alkylation of lactic acid with the assistance of 8-aminoquinoline auxiliary. A wide range of alkyl iodides bearing b-hydrogen atoms are compatible with the reaction conditions, providing a practical and straightforward alternative to access chiral a-hydroxy acids (AHAs). The new reactions have been applied for the synthesis of isotope-labeled AHAs and a sugarcont...

Synthesis of β-C-D-galactosyl D- and L-alanines is carried out via a highly stereoselective Grignard reaction of glycosyl iodides, Sharpless dihydroxylation and S(N)2 displacement of the corresponding mesylate or tosylate. Alternatively, attempted triflation of the intermediate alcohols triggers a stereoselective debenzylative cyclization leading to interesting bicyclic trans-fused compounds.

The reaction of various cyclic alkenyl iodides with i-PrMgCl.LiCl produces the corresponding alkenylmagnesium reagents under mild conditions. After reaction with various electrophiles, like allylic halides, disulfides, aldehydes and acid chlorides, the expected products are obtained in 53-91% yield. Remarkably, the mild conditions of the I/Mg-exchange tolerate the presence of sensitive diene fu...

Cu(I)-diamine complexes were found to catalyse the trifluoromethylation of aryl iodides. In the presence of a small amount of CuX (X = Cl, Br, I) and 1,10-phenanthroline (phen), the cross-coupling reactions of iodoarenes with trifluoromethylsilanes proceeded smoothly to afford trifluoromethylated aromatics in good yields.

We developed a palladium-catalyzed carbonylative Sonogashira reaction with aryl triazenes and alkynes as substrates and methanesulfonic acid as the additive. A series of α,β-ynones were synthesized by this alternative procedure. Notably, bromides, iodides and hydroxyl groups could be well-tolerated under these reaction conditions.

The treatment of aryl iodides with tris(trimethylsilyl)silane in the presence of Pd(P(tBu)(3))(2) and the Hünig base leads to the formation of hypersilylated aromatic products in good to excellent yields without cleavage of weak Si-Si bonds under mild conditions.

An efficient La2O3-catalyzed new route for the carbon-carbon bond formation in particular, symmetrical and unsymmetrical biphenyls has been developed, which proceeds through carbon-carbon coupling reaction of aryl iodides with boronic acids. The reaction provided the desired products in moderate-to-good yields with a wide range of functional group tolerance.

A Ni-catalyzed asymmetric reductive cross-coupling of heteroaryl iodides and α-chloronitriles has been developed. This method furnishes enantioenriched α,α-disubstituted nitriles from simple organohalide building blocks. The reaction tolerates a variety of heterocyclic coupling partners, including pyridines, pyrimidines, quinolines, thiophenes, and piperidines. The reaction proceeds under mild ...