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

Kerry Ann Green; Aaron P. Honeycutt; Sierra R. Ciccone; Kyle A. Grice; Andreas Baur; Jeffrey L. Petersen; Jessica M. Hoover

doi:10.1021/acscatal.2c06015

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

Kerry Ann Green, Aaron P. Honeycutt, Sierra R. Ciccone, Kyle A. Grice, Andreas Baur, Jeffrey L. Petersen, Jessica M. Hoover

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

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 C-S bonds. We anticipate that this redox transmetalation step may be relevant to other coupling reactions that employ silver salts as additives.

Original language	English (US)
Pages (from-to)	6375-6381
Number of pages	7
Journal	ACS Catalysis
Volume	13
Issue number	9
DOIs	https://doi.org/10.1021/acscatal.2c06015
State	Published - May 5 2023
Externally published	Yes

Bibliographical note

Funding Information:
The authors are grateful to the NIH (1R15GM126514-01) and West Virginia University for financial support of this work. NMR spectroscopy (CHE-1228336) and X-ray diffraction (CHE-1336071) facilities were partially supported by the NSF. The authors thank Melanie Sanford for helpful discussions on related nickelacycle systems.

Publisher Copyright:
© 2023 The Authors. Published by American Chemical Society

Keywords

cross-coupling
metallacycle
nickel
redox
reductive elimination
silver
transmetalation

PubMed: MeSH publication types

Journal Article

Publisher link

10.1021/acscatal.2c06015

Find It

Find It at U of M Libraries

Cite this

@article{9fccd80db3aa4584b331ca115946730a,

title = "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 C-S bonds. We anticipate that this redox transmetalation step may be relevant to other coupling reactions that employ silver salts as additives.",

keywords = "cross-coupling, metallacycle, nickel, redox, reductive elimination, silver, transmetalation",

author = "Green, {Kerry Ann} and Honeycutt, {Aaron P.} and Ciccone, {Sierra R.} and Grice, {Kyle A.} and Andreas Baur and Petersen, {Jeffrey L.} and Hoover, {Jessica M.}",

note = "Funding Information: The authors are grateful to the NIH (1R15GM126514-01) and West Virginia University for financial support of this work. NMR spectroscopy (CHE-1228336) and X-ray diffraction (CHE-1336071) facilities were partially supported by the NSF. The authors thank Melanie Sanford for helpful discussions on related nickelacycle systems. Publisher Copyright: {\textcopyright} 2023 The Authors. Published by American Chemical Society",

year = "2023",

month = may,

day = "5",

doi = "10.1021/acscatal.2c06015",

language = "English (US)",

volume = "13",

pages = "6375--6381",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - A Redox Transmetalation Step in Nickel-Catalyzed C-C Coupling Reactions

AU - Green, Kerry Ann

AU - Honeycutt, Aaron P.

AU - Ciccone, Sierra R.

AU - Grice, Kyle A.

AU - Baur, Andreas

AU - Petersen, Jeffrey L.

AU - Hoover, Jessica M.

N1 - Funding Information: The authors are grateful to the NIH (1R15GM126514-01) and West Virginia University for financial support of this work. NMR spectroscopy (CHE-1228336) and X-ray diffraction (CHE-1336071) facilities were partially supported by the NSF. The authors thank Melanie Sanford for helpful discussions on related nickelacycle systems. Publisher Copyright: © 2023 The Authors. Published by American Chemical Society

PY - 2023/5/5

Y1 - 2023/5/5

N2 - 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 C-S bonds. We anticipate that this redox transmetalation step may be relevant to other coupling reactions that employ silver salts as additives.

AB - 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 C-S bonds. We anticipate that this redox transmetalation step may be relevant to other coupling reactions that employ silver salts as additives.

KW - cross-coupling

KW - metallacycle

KW - nickel

KW - redox

KW - reductive elimination

KW - silver

KW - transmetalation

UR - http://www.scopus.com/inward/record.url?scp=85156235708&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85156235708&partnerID=8YFLogxK

U2 - 10.1021/acscatal.2c06015

DO - 10.1021/acscatal.2c06015

M3 - Article

C2 - 37180967

AN - SCOPUS:85156235708

SN - 2155-5435

VL - 13

SP - 6375

EP - 6381

JO - ACS Catalysis

JF - ACS Catalysis

IS - 9

ER -

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

Abstract

Bibliographical note

Keywords

PubMed: MeSH publication types

Publisher link

Find It

Other files and links

Fingerprint

Cite this