Nickel-catalyzed coupling reaction of lithium organoborates and aryl mesylates possessing an electron withdrawing group

Well-defined nickel and palladium precatalysts for cross-coupling

“…91). These results were extended by Mizojiri et al 92,93 who showed that non-classical electrophiles, including aryl mesylates, tosylates and allyl carbonates, could be coupled with lithium arylborates under mild conditions with [(PPh 3 ) 2 NiCl 2 ]. Recently, Percec and co-workers 89,94 demonstrated that [(PPh 3 ) 2 NiCl 2 ] can effectively perform Suzuki–Miyaura reactions with both pseudohalides and phenol derivatives, such as sulfamates and carbamates, which can be used as directing groups in C–H functionalization reactions.…”

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

“…69 Higher yields were obtained using lithium arylborates. 70 This reaction was, however, restricted to mesylates and tosylates containing EWGs. Recently, Monteiro and co-workers 71 have reported the use of the NiCl 2 (PCy 3 ) 2 catalyst in the SM cross-coupling reaction of a variety of aryl tosylates with arylboronic acid under mild reaction conditions (Scheme 28).…”

State‐of‐the‐Art in Metal‐Catalyzed Cross‐Coupling Reactions of Organoboron Compounds with Organic Electrophiles

“…Similar to the Love group, they have also discovered that directing groups can significantly facilitate the cross-coupling process without the necessity of any additives. In addition to imines, they have also learned that pyridine (79), pyrimidine (80), pyrazole (81), oxazole (82), quinoline (83), and isoquinoline (84) are all suitable directing groups to accelerate cross-couplings of aryl fluorides (Scheme 2.13).…”

“…Moreover, due to their existence as an inseparable mixture with boroxines, the weighing of boronic acids is usually less accurate. [81,82], and neutral boronic ester derivatives will not be discussed in detail and only the more recently developed preactivated borates will be described in the following section. Ni-catalyzed Suzuki-Miyaura cross-coupling reaction [55a, 56a, 84k], allowing cheaper and more stable electrophiles to be utilized.…”