Abstract
Transition-metal catalysis has been consequential in enabling carbon–heteroatom bond-forming
reactions. Recent breakthroughs in Ni-catalyzed cross-couplings have offered competitive
and, in some cases, superior reactivity to Pd- or Cu-based processes. Amidst the ongoing
renaissance in this field, the Ni-catalyzed C–O cross-coupling of alcohols and (hetero)aryl
(pseudo)halides has surfaced as an effective strategy for the synthesis of (hetero)aryl
ethers. Methodologies to achieve such transformations tend to rely on one of three
catalytic approaches: (i) thermal conditions often accompanied by ancillary ligand
design tailored for Ni catalysis; (ii) the synergistic combination of photoredox and
Ni catalysis; or (iii) electrochemically driven Ni catalysis. In some instances, these
protocols have provided access to expanded C–O cross-coupling substrate scope, including
the use of inexpensive and abundant electrophile coupling partners (e.g., (hetero)aryl
chlorides). This Short Review aims to summarize recent progress in the development
of Ni-catalyzed O-arylations of primary, secondary, and tertiary aliphatic alcohols, as well as phenols,
with (hetero)aryl electrophiles.
1 Introduction
2 Thermally Promoted Ni C–O Cross-Coupling
2.1 Primary and Secondary Aliphatic Alcohols
2.2 Tertiary Aliphatic Alcohols
2.3 Phenols
3 Photochemically Promoted Ni C–O Cross-Coupling
3.1 Primary and Secondary Aliphatic Alcohols
3.2 Phenols
4 Electrochemically Promoted Ni C–O Cross-Coupling
4.1 Primary and Secondary Aliphatic Alcohols
5 Conclusions and Outlook
Key words
nickel catalysis -
O-arylation - synthesis - cross-coupling - etherification
