Organoboronic acids, some of the most common and widely used organoboron compounds, have not yet been used in the cobalt-catalyzed cross coupling reactions, despite cobalt demonstrating good reactivity with zinc reagents, Grignard reagents, and metal organoborates that are formed by n-butyl lithium or alkaline metal alkoxide salts and organoboron esters. Herein, a highly efficient and practical cobalt-catalyzed coupling reaction of aryl/alkenyl boronic acids and alkynyl chloride under mild reaction conditions is reported. The advantages of the organoboronic acids, along with a broad functional group compatibility and the reaction's tolerance to moisture and air, enable this reaction to be a synthetically useful protocol for the construction of a C(sp2)–C(sp) bond. Lastly, the synthesis of two natural products and a key intermediate of roxadustat was effectively accomplished using the methodology to construct the critical alkynyl–aryl bond. 

Co-Catalyzed Suzuki–Miyaura Coupling of Organoboronic Acids and Alkynyl Chlorides Using Potassium Bicarbonate as Base

The Negishi cross-coupling reactions involves the application of organozinc reagents and is a highly versatile reaction in synthetic organic chemistry. The transmetallation step plays a pivotal role in the mechanism of these types of cross-coupling reactions. Herein, we present our mechanistic investigations, indicating, that higher-order zincates are the transmetallating active species in Pd- and Ni-catalyzed Negishi cross-coupling reactions. These findings are supported by halide salt addition experiments and by obtaining a single X-ray crystal structure of the solid monoaryl higher-order zincate [1-NaphthylZnX3]2-Mg(THF)22+. The procedure developed in this work was further applied to the synthesis of various monoaryl higher-order zincates, after which their synthetic usefulness in terms of high reactivity towards transmetallation in Negishi cross-couplings, as well as stability, was exemplified in several reactions.

Atroposelective NiII-Catalyzed Cross-Coupling Reactions Enable a Deeper Understanding of Negishi Couplings: Isolation and Application of Solid Aryl Higher-Order Zincates.

Carbonyl groups and alkenes are ubiquitous in organic chemistry─present in target molecules as well as versatile handles for conversion into other functional groups. Whereas the coupling of the α position of a carbonyl compound with an alkenyl electrophile represents an attractive approach to uniting these useful functionalities, to date there have been few reports of catalytic asymmetric variants of this bond construction. Most of the progress to date has involved cyclic carbonyl compounds (obviates the issue of controlling the E/Z geometry of the nucleophile) and the generation of quaternary stereocenters (obviates undesired side reactions of the β,γ-unsaturated carbonyl product, such as racemization or isomerization to the more stable α,β-unsaturated carbonyl compound). Herein, we establish that a chiral nickel catalyst can couple acyclic racemic Reformatsky-type reagents (α-zincated amides) with alkenyl halides to generate β,γ-unsaturated amides that bear a tertiary α stereocenter with good enantioselectivity and good yield. The products can be transformed into other useful families of enantioenriched compounds, including intermediates in total synthesis. Mechanistic studies are consistent with a nickel(0)/nickel(II) pathway for asymmetric carbon-carbon bond formation.

Nickel-Catalyzed Asymmetric α-Alkenylations of Acyclic Amides that Provide Tertiary Stereocenters

Enhancement of nitrogen content in fullerene soot via radical decarboxylative coupling under catalytic and noncatalytic conditions

Transition metal-catalyzed carbon–carbon bonds formation is a fundamental process and has attracted much attention in the synthetic chemistry community over the past decades. This chapter summarizes the recent advances (from 2012 until 2022) in nickel-catalyzed C-C coupling reactions, covering the formation of C(sp2)-C(sp2) bond, C(sp2)-C(sp3) bond, and C(sp3)-C(sp3) bond, as well as the corresponding innovative strategies and mechanisms are discussed in detail, with an emphasis on nickel’s unique properties. 

Recent Advances in Nickel-Catalyzed C-C Cross-Coupling

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Recent Advances in Nickel-Catalyzed C-C Cross-Coupling