Working Paper
Authors
- Maximilian Palkowitz Scripps Research ,
- Gabriele Laudadio Scripps Research ,
- Simon Kolb Scripps Research ,
- Jin Choi Scripps Research ,
- Martins Oderinde Bristol Myers Squibb Research and Development ,
- Tamara Ewing Scripps Research ,
- Philippe Bolduc Biogen Inc. ,
- TeYu Chen Biogen Inc. ,
- Hao Zhang Bristol Myers Squibb Research and Development ,
- Peter Cheng Bristol Myers Squibb Research and Development ,
- Benxiang Zhang Scripps Research ,
- Michael Mandler Bristol Myers Squibb Research and Development ,
- Jeremy Richter Bristol Myers Squibb Research and Development ,
- Michael Collins Pfizer Pharmaceuticals, Oncology Medicinal Chemistry Department ,
- Ryan Schioldager Pfizer Pharmaceuticals, Oncology Medicinal Chemistry Department ,
- Murali Dhar Bristol Myers Squibb Research and Development ,
- Benjamin Vokits Bristol Myers Squibb Research and Development ,
- Yeheng Zhu Bristol Myers Squibb Research and Development ,
- Pierre-Georges Echeverria Minakem ,
- Michael Poss Bristol Myers Squibb Research and Development ,
- Scott Shaw Bristol Myers Squibb Research and Development ,
- Sebastian Clementson LEO Pharma ,
- Nadia Petersen LEO Pharma ,
- Pavel Mykhailiuk Enamine Ltd ,
- Phil Baran
Scripps Research
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, technical grade solvents, an inexpensive ligand and Ni source, 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 mg-based synthesis to decagram recirculating flow is presented
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Supplementary material

Supporting Information
Procedures and Spectral Data