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Overcoming Limitations in Decarboxylative Arylation via Ag–Ni Electrocatalysis

Palkowitz, Maximilian D. ; Laudadio, Gabriele ; Kolb, Simon ; Choi, Jin ; Oderinde, Martins S. ; Ewing, Tamara El-Hayek ; Bolduc, Philippe N. ; Chen, TeYu ; Zhang, Hao and Cheng, Peter T. W. , et al. (2022) In Journal of the American Chemical Society 144(38). p.17709-17720
Abstract
A useful protocol for achieving decarboxylative cross-coupling (DCC) of redox-active esters (RAE, isolated or generated in situ) and halo(hetero)arenes is reported. This pragmatically focused study employs a unique Ag–Ni electrocatalytic platform to overcome numerous limitations that have plagued this strategically powerful transformation. In its optimized form, coupling partners can be combined in a surprisingly simple way: open to the air, using technical-grade solvents, an inexpensive ligand and Ni source, and substoichiometric AgNO3, proceeding at room temperature with a simple commercial potentiostat. Most importantly, all of the results are placed into context by benchmarking with state-of-the-art methods. Applications are presented... (More)
A useful protocol for achieving decarboxylative cross-coupling (DCC) of redox-active esters (RAE, isolated or generated in situ) and halo(hetero)arenes is reported. This pragmatically focused study employs a unique Ag–Ni electrocatalytic platform to overcome numerous limitations that have plagued this strategically powerful transformation. In its optimized form, coupling partners can be combined in a surprisingly simple way: open to the air, using technical-grade solvents, an inexpensive ligand and Ni source, and substoichiometric AgNO3, proceeding at room temperature with a simple commercial potentiostat. Most importantly, all of the results are placed into context by benchmarking with state-of-the-art methods. Applications are presented that simplify synthesis and rapidly enable access to challenging chemical space. Finally, adaptation to multiple scale regimes, ranging from parallel milligram-based synthesis to decagram recirculating flow is presented. (Less)
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publishing date
type
Contribution to journal
publication status
published
in
Journal of the American Chemical Society
volume
144
issue
38
pages
12 pages
publisher
The American Chemical Society (ACS)
external identifiers
  • scopus:85138479259
ISSN
1520-5126
DOI
10.1021/jacs.2c08006
language
Unknown
LU publication?
no
additional info
PMID: 36106767
id
0d11a5da-d61d-446f-bb72-0a8dd7253620
date added to LUP
2025-08-06 19:28:49
date last changed
2025-08-12 13:21:06
@article{0d11a5da-d61d-446f-bb72-0a8dd7253620,
  abstract     = {{A useful protocol for achieving decarboxylative cross-coupling (DCC) of redox-active esters (RAE, isolated or generated in situ) and halo(hetero)arenes is reported. This pragmatically focused study employs a unique Ag–Ni electrocatalytic platform to overcome numerous limitations that have plagued this strategically powerful transformation. In its optimized form, coupling partners can be combined in a surprisingly simple way: open to the air, using technical-grade solvents, an inexpensive ligand and Ni source, and substoichiometric AgNO3, proceeding at room temperature with a simple commercial potentiostat. Most importantly, all of the results are placed into context by benchmarking with state-of-the-art methods. Applications are presented that simplify synthesis and rapidly enable access to challenging chemical space. Finally, adaptation to multiple scale regimes, ranging from parallel milligram-based synthesis to decagram recirculating flow is presented.}},
  author       = {{Palkowitz, Maximilian D. and Laudadio, Gabriele and Kolb, Simon and Choi, Jin and Oderinde, Martins S. and Ewing, Tamara El-Hayek and Bolduc, Philippe N. and Chen, TeYu and Zhang, Hao and Cheng, Peter T. W. and Zhang, Benxiang and Mandler, Michael D. and Blasczak, Vanna D. and Richter, Jeremy M. and Collins, Michael R. and Schioldager, Ryan L. and Bravo, Martin and Dhar, T. G. Murali and Vokits, Benjamin and Zhu, Yeheng and Echeverria, Pierre-Georges and Poss, Michael A. and Shaw, Scott A. and Clementson, Sebastian and Petersen, Nadia Nasser and Mykhailiuk, Pavel K. and Baran, Phil S.}},
  issn         = {{1520-5126}},
  language     = {{und}},
  number       = {{38}},
  pages        = {{17709--17720}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{Journal of the American Chemical Society}},
  title        = {{Overcoming Limitations in Decarboxylative Arylation via Ag–Ni Electrocatalysis}},
  url          = {{http://dx.doi.org/10.1021/jacs.2c08006}},
  doi          = {{10.1021/jacs.2c08006}},
  volume       = {{144}},
  year         = {{2022}},
}