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Synfacts 2022; 18(09): 0977
DOI: 10.1055/s-0041-1738683
DOI: 10.1055/s-0041-1738683
Metals in Synthesis
Tungsten-Catalyzed Alkene Isomerization/Hydrocarbonylative Cyclization
Jankins TC,
Bell WC,
Zhang Y,
Qin Z.-Y,
Chen JS,
Gembicky M,
Liu P,
*,
Engle KM.
*
University of Pittsburgh and The Scripps Research Institute, La Jolla, USA
Low-Valent Tungsten Redox Catalysis Enables Controlled Isomerization and Carbonylative Functionalization of Alkenes.
Nat. Chem. 2022;
14: 632-639
Low-Valent Tungsten Redox Catalysis Enables Controlled Isomerization and Carbonylative Functionalization of Alkenes.
Nat. Chem. 2022;
14: 632-639
Significance
A tungsten-catalyzed isomerization of terminal alkenes to unactivated internal positions followed by subsequent hydrocarbonylation with CO is reported. This work addresses common challenges associated with the regioselectivity of tandem alkene isomerization/functionalization reactions.
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Comment
Experimental and DTF studies were carried out to elucidate the mechanism. Key to this transformation is the six- to seven-coordinate geometry changes present in the W(0)/W(II) redox cycle and the presence of a conformationally flexible directing group that allows for isomerization to take place.
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Publication History
Article published online:
18 August 2022
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