16606-00-1Relevant articles and documents
Palladium-catalyzed Suzuki cross-coupling of phenylhydrazine or (phenylsulfonyl)hydrazine
Li, Yahui,Liu, Wei,Tian, Qingshan,Yang, Qing,Kuang, Chunxiang
, p. 3307 - 3312 (2014)
The palladium-catalyzed Suzuki cross-coupling of phenylhydrazine or (phenylsulfonyl)hydrazine was developed for the preparation of biaryl compound in high yields. Moreover, these hydrazines were also used in other cross-coupling reactions, and a possible pathway of this reaction was examined. Copyright
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Bly,R.S. et al.
, p. 35 - 54 (1976)
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'Awaken' aryl sulfonyl fluoride: a new partner in the Suzuki-Miyaura coupling reaction
Ding, Chengrong,Guan, Chenfei,Miao, Huihui,Zhang, Guofu,Zhao, Yiyong
supporting information, p. 3560 - 3564 (2022/03/07)
An example of the activation of the -SO2F group, which is traditionally considered a stable group even in the presence of a transition metal, is described using a novel partner in the Suzuki-Miyaura coupling reaction catalyzed by Pd(OAc)2 and Ruphos as ligands. The products showed good to outstanding yields and broad functional group compatibility under optimal conditions. The sequential synthesis of non-symmetric terphenyls and the gram grade process highlight the approach's synthetic utility. DFT calculations have shown that Pd0 prefers to insert between C-S bonds rather than S-F bonds. This journal is
Cobalt-Catalyzed Coupling of Aryl Chlorides with Aryl Boron Esters Activated by Alkoxides
Tailor, Sanita B.,Manzotti, Mattia,Smith, Gavin J.,Davis, Sean A.,Bedford, Robin B.
, p. 3856 - 3866 (2021/04/07)
The cobalt-catalyzed Suzuki biaryl cross-coupling of aryl chloride substrates with aryl boron reagents, activated with more commonly used bases, remained a significant unmet challenge in the race to replace platinum group metal catalysts with Earth-abundant metal alternatives. We now show that this highly desirable process can be realized using alkoxide bases, provided the right counterion is employed, strict stoichiometric control of the base is maintained with respect to the aryl boron reagent, and the correct boron ester is selected. Potassium tert-butoxide works well, but any excess of the base first inhibits and then poisons the catalyst. Lithium tert-butoxide performs very poorly, while even catalytic amounts of lithium additives also poison the catalyst. Meanwhile, a neopentane diol-based boron ester is required for best performance. As well as delivering this sought-after transformation, we have undertaken detailed mechanistic and computational investigations to probe the possible mechanism of the reaction and help explain the unexpected experimental observations.
Cobalt-catalyzed C(sp2)?CN bond activation: Cross-electrophile coupling for biaryl formation and mechanistic insight
Dorval, Céline,Tricoire, Maxime,Begouin, Jeanne-Marie,Gandon, Vincent,Gosmini, Corinne
, p. 12819 - 12827 (2020/11/18)
Herein, we report a cross-electrophile coupling of benzonitrile derivatives and aryl halides with a simple cobalt-based catalytic system under mild conditions to form biaryl compounds. Even though the cobalt catalyst is able to activate the C(sp2)?CN bond alone, the use of the AlMe3 Lewis acid enhances the reactivity of benzonitriles and improves the cross-selectivity with barely any influence on the functional group compatibility. X-ray structure determination of an original low-valent cobalt species combined with catalytic and stoichiometric reactions reveals a catalytically active cobalt(I) species toward the aryl halide partner. On the other hand, experimental insights, including cyclic voltammetry experiments, suggest the involvement of a cobalt complex of a lower oxidation state to activate the benzonitrile derivative. Finally, density functional theory calculations support the proposed mechanistic cycle involving two low-valent cobalt species of different oxidation states to perform the reaction.
