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Synlett 2021; 32(15): 1484-1491
DOI: 10.1055/a-1503-6330
DOI: 10.1055/a-1503-6330
synpacts
C–O-Selective Cross-Coupling of Chlorinated Phenol Derivatives
This material is based upon work supported by the National Science Foundation (CAREER: CHE-1848090). Calculations were performed on Comet at SDSC through XSEDE (CHE-170089), which is supported by NSF (ACI-1548562).
Abstract
Chemoselective cross-coupling of phenol derivatives is valuable for generating products that retain halides. Here we discuss recent developments in selective cross-couplings of chloroaryl phenol derivatives, with a particular focus on reactions of chloroaryl tosylates. The first example of a C–O-selective Ni-catalyzed Suzuki–Miyaura coupling of chloroaryl tosylates is discussed in detail.
1 Introduction
2 Density Functional Theory Studies on Oxidative Addition at Nickel(0)
3 Stoichiometric Oxidative Addition Studies
4 Development of a Tosylate-Selective Suzuki Coupling
5 Conclusion and Outlook
Key words
nickel catalysis - cross-coupling - oxidative addition - chemoselectivity - density functional theory - Suzuki–Miyaura couplingPublication History
Received: 27 April 2021
Accepted: 08 May 2021
Accepted Manuscript online:
08 May 2021
Article published online:
16 June 2021
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44 Interestingly, a bipyridine ligand was recently shown to promote C–O-selective reaction of Ni with a chloroaryl tosylate in the presence of Pd as part of a cross-electrophile coupling; see ref. 25.
For examples, see:
For Cl vs. OTf selectivity using Pd and phosphine ligands, see:
For examples of Fe-catalyzed Kumada couplings that are selective for reaction at Cl, see:
For examples of Ru-catalyzed direct arylations that are selective for reaction at Cl, see:
For selected reviews, see:
For selected reviews, see:
For examples of Ni-catalyzed divergent selectivity between activation of C(aryl)-O and C(acyl)-O bonds of aryl esters, where selectivity depends on the ligation state of nickel, see:
For evaluation or use of PMe3 in other types of Ni-catalyzed couplings, see:
For the use of PMe3 as a ligand for Pd-catalyzed cross-couplings, see: