Regioselective molybdenum-catalyzed allylic substitution of tertiary allylic electrophiles: methodology development and applications

The first molybdenum-catalyzed allylic sulfonylation of tertiary allylic electrophiles is described. The method employs a readily accessible catalyst (Mo(CO) 6 /2,2′-bipyridine, both are commercially available) and represents the first example of the use of a group 6 transition metal-catalyst for al...

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Veröffentlicht in:Chemical science (Cambridge) Jg. 11; H. 21; S. 5481 - 5486
Hauptverfasser: Salman, Muhammad, Xu, Yaoyao, Khan, Shahid, Zhang, Junjie, Khan, Ajmal
Format: Journal Article
Sprache:Englisch
Veröffentlicht: CAMBRIDGE Royal Soc Chemistry 07.06.2020
Royal Society of Chemistry
The Royal Society of Chemistry
Schlagworte:
Catalysts
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Cross coupling
Molybdenum
NMR
Nuclear magnetic resonance
Physical Sciences
Regioselectivity
Science & Technology
Substrates
Transition metals
CHIRAL SULFONES
ASYMMETRIC-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
VINYLETHYLENE CARBONATES
DECARBOXYLATIVE CYCLOADDITION
ALKYLATION
CONSTRUCTION
QUATERNARY STEREOCENTERS
SULFONYL HYDRAZIDES
STEREOGENIC CENTERS
ISSN:2041-6520, 2041-6539
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Zusammenfassung:The first molybdenum-catalyzed allylic sulfonylation of tertiary allylic electrophiles is described. The method employs a readily accessible catalyst (Mo(CO) 6 /2,2′-bipyridine, both are commercially available) and represents the first example of the use of a group 6 transition metal-catalyst for allylic sulfonylation of substituted tertiary allylic electrophiles to form carbon-sulfur bonds. This atom economic and operationally simple methodology is characterized by its relatively mild conditions, wide substrate scope, and excellent regioselectivity profile, thus unlocking a new platform to forge sulfone moieties, even in the context of late-stage functionalization and providing ample opportunities for further derivatization through traditional Suzuki cross-coupling reactions. The first general example of Mo-catalyzed allylic sulfonylation of tertiary allylic electrophile provides an efficient way to forge sulfone moieties, and providing ample opportunities for further transformation through traditional Suzuki cross-coupling.
Bibliographie:H
1
Electronic supplementary information (ESI) available: For detailed experimental procedures, characterization data of all of the new compounds, and copies of
13
C NMR spectra of the substrates and products. See DOI
10.1039/d0sc01763a
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These authors contributed equally.
ISSN:2041-6520
2041-6539
DOI:10.1039/d0sc01763a