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Synfacts 2024; 20(11): 1156
DOI: 10.1055/s-0043-1775167
DOI: 10.1055/s-0043-1775167
Metals in Synthesis
Nickel-Catalyzed Cross-Coupling of Cyclic Sulfones and Grignard Reagents
Nolla-Saltiel R,
Ariki ZT,
Schiele S,
Alpin J,
Tahara Y,
Yokogawa D,
Nambo M,
*,
Crudden CM.
*
Queen’s University, Kingston, Canada and Nagoya University, Japan
Enantiospecific Cross-Coupling of Cyclic Alkyl Sulfones.
Nat. Chem. 2024;
16: 1445-1452
DOI: 10.1038/s41557-024-01594-x
Enantiospecific Cross-Coupling of Cyclic Alkyl Sulfones.
Nat. Chem. 2024;
16: 1445-1452
DOI: 10.1038/s41557-024-01594-x
Significance
Nickel-catalyzed ring-opening arylation of α-aryl cyclic sulfones with aryl Grignard reagents as nucleophiles is reported. The reaction can be carried out in an enantiospecific fashion by using enantioenriched sulfones (not shown).
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Comment
Experimental studies and DFT calculations support the shown catalytic cycle. The use of a preformed nickel(II) catalyst was the key to minimize competing β-hydride elimination. The cross-coupled products were also treated with electrophiles other than MeI, affording various sulfone products in good yields (not shown).
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Publication History
Article published online:
16 October 2024
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