Download PDF
Synfacts 2024; 20(11): 1156
DOI: 10.1055/s-0043-1775167
Metals in Synthesis

Nickel-Catalyzed Cross-Coupling of Cyclic Sulfones and Grignard Reagents

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare
,
Sergiu Bicic
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
CrossrefPubMedSearch in Google Scholar
› Further Information
 
 PDF Download Permissions and Reprints

Key words

cross-coupling - Grignard reagents - nickel catalysis - sulfones

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).


#

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).


#
#

Publication History

Article published online:
16 October 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany


   Permissions and Reprints