2023
DOI: 10.1021/acscatal.2c06015
|View full text |Cite
|
Sign up to set email alerts
|

A Redox Transmetalation Step in Nickel-Catalyzed C–C Coupling Reactions

Abstract: Ni-catalyzed C−H functionalization reactions are becoming efficient routes to access a variety of functionalized arenes, yet the mechanisms of these catalytic C−C coupling reactions are not well understood. Here, we report the catalytic and stoichiometric arylation reactions of a nickel(II) metallacycle. Treatment of this species with silver(I)−aryl complexes results in facile arylation, consistent with a redox transmetalation step. Additionally, treatment with electrophilic coupling partners generates C−C and… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1
1

Citation Types

0
2
0

Year Published

2023
2023
2024
2024

Publication Types

Select...
5

Relationship

0
5

Authors

Journals

citations
Cited by 5 publications
(2 citation statements)
references
References 84 publications
0
2
0
Order By: Relevance
“…is enhanced in the isolated difunctionalized product compared with that of the monofunctionaled product through both the preferential reaction of one regioisomer of the intermediate σ-aryl complex and chromatography during separation. Because complex 4a is ambiphilic, the reverse addition of the coupling partners of MeI to form complex 6a followed by redox-active transmetalation organometallic reagent MesAg generated the opposite regioisomer of 11a’ exclusively in 34% yield over two steps, which further highlights the potential to expand chemical space from a single starting point ( 51 ).…”
Section: Reactivitymentioning
confidence: 97%
“…is enhanced in the isolated difunctionalized product compared with that of the monofunctionaled product through both the preferential reaction of one regioisomer of the intermediate σ-aryl complex and chromatography during separation. Because complex 4a is ambiphilic, the reverse addition of the coupling partners of MeI to form complex 6a followed by redox-active transmetalation organometallic reagent MesAg generated the opposite regioisomer of 11a’ exclusively in 34% yield over two steps, which further highlights the potential to expand chemical space from a single starting point ( 51 ).…”
Section: Reactivitymentioning
confidence: 97%
“…Because numerous researchers have now entered this research field in a very short period of time, we gave up on continuing this research. Not only synthetic chemists but also theoretical chemists ,, and organometallic chemists have become interested in the Ni/N,N-bidentate chelation system because the reactions were first proposed to include an unstable high-valence Ni­(IV) and/or Ni­(III) species.…”
Section: Use Of the Nn-bidentate Directing Group In Ni-catalyzed C–h ...mentioning
confidence: 99%