Photocatalytic dehydroxymethylative arylation by synergistic cerium and nickel catalysis

Journal of the American Chemical Society

Under mild reaction conditions with inexpensive cerium and nickel catalysts, easily accessible free alcohols can now be utilized as operationally simple and robust carbon pronucleophiles in selective C(sp3)–C(sp2) cross-couplings. Facilitated by automated high-throughput experimentation, sterically encumbered benzoate ligands have been identified for robust cerium complexes, enabling the synergistic cooperation of cerium catalysis in the emerging metallaphotoredox catalysis. A broad range of free alcohols and aromatic halides can be facilely employed in this transformation, representing a new paradigm for the C(sp3)–C(sp2) bond construction between free alcohols and aryl halides with the extrusion of formaldehyde. Moreover, mechanistic investigations have been conducted, leading to the identification of a tribenzoate cerium(III) complex as a viable intermediate.

For details:

Photocatalytic dehydroxymethylative arylation by synergistic cerium and nickel catalysis

Yuegang Chen 1, Xin Wang 1, Xu He 1, Qing An 1 and Zhiwei Zuo 2

1 School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China

2 State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

For more information about Chemspeed solutions:

FLEX ISYNTH

ISYNTH AI

ISYNTH REACTSCREEN

J. Am. Chem. Soc. 2021, 143, 13, 4896–4902
https://doi.org/10.1021/jacs.1c00618
Copyright © 2021 American Chemical Society

For details please contact [email protected]

July 20, 2021