Coupling of aromatic aldehydes with aryl halides in the presence of nickel catalysts with diazabutadiene ligands

Nickel-Catalyzed Asymmetric Addition of Aromatic Halides to Ketones: Highly Enantioselective Synthesis of Chiral 2,3-Dihydrobenzofurans Containing a Tertiary Alcohol

“…9 Unfortunately, no enantioselectivity was observed when using chiral bisoxazoline as ligand. Since then, Mashima, 10 Voskoboynikov, 11 and Weix 12 reported their excellent works on aryl halo ketone addition and greatly expanded the scope of aryl halides and aldehydes. Recently, Itoh and Yamaguchi achieved the first enantioselective addition of aryl halide to aldehydes 13 but only afforded the chiral diarylmethanol in 29% yield with 46% ee.…”

Nickel-Catalyzed Addition of Aryl Bromides to Aldehydes To Form Hindered Secondary Alcohols

“… 4 , 5 The coupling of aryl iodides with aldehydes in the presence of a reducing agent can be catalyzed by Cr/Ni, 6 Co, 7 and Rh. 8 , 9 Aryl bromides are an order of magnitude more abundant than aryl iodides ( Scheme 1 ), 10 but their use in aldehyde arylation remains underdeveloped 11 − 13 and a topic of current interest. 14 , 15 …”

“…A catalytic method for the direct addition of aryl halides to aldehydes would be ideal, but relatively few couplings of this type have been reported. , The coupling of aryl iodides with aldehydes in the presence of a reducing agent can be catalyzed by Cr/Ni, Co, and Rh. , Aryl bromides are an order of magnitude more abundant than aryl iodides (Scheme ), but their use in aldehyde arylation remains underdeveloped − and a topic of current interest. , …”