Journal
SYNTHESIS-STUTTGART
Volume 49, Issue 15, Pages 3323-3336Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1589046
Keywords
Zweifel olefination; coupling; boronic esters; alkenes; transition-metal-free; enantiospecific
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Funding
- EPSRC [EP/I038071/1]
- European Research Council [670668]
- Engineering and Physical Sciences Research Council [EP/I038071/1] Funding Source: researchfish
- European Research Council (ERC) [670668] Funding Source: European Research Council (ERC)
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The Zweifel olefination is a powerful method for the stereo-selective synthesis of alkenes. The reaction proceeds in the absence of a transition-metal catalyst, instead taking place by iodination of vinyl boronate complexes. Pioneering studies into this reaction were reported in 1967 and this short review summarizes developments in the field over the past 50 years. An account of how the Zweifel olefination was modified to enable the coupling of robust and air-stable boronic esters is presented followed by a summary of current state of the art developments in the field, including stereodivergent olefination and alkynylation. Finally, selected applications of the Zweifel olefination in targetoriented synthesis are reviewed.
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