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Kinetically controlled E-selective catalytic olefin metathesis.


ABSTRACT: A major shortcoming in olefin metathesis, a chemical process that is central to research in several branches of chemistry, is the lack of efficient methods that kinetically favor E isomers in the product distribution. Here we show that kinetically E-selective cross-metathesis reactions may be designed to generate thermodynamically disfavored alkenyl chlorides and fluorides in high yield and with exceptional stereoselectivity. With 1.0 to 5.0 mole % of a molybdenum-based catalyst, which may be delivered in the form of air- and moisture-stable paraffin pellets, reactions typically proceed to completion within 4 hours at ambient temperature. Many isomerically pure E-alkenyl chlorides, applicable to catalytic cross-coupling transformations and found in biologically active entities, thus become easily and directly accessible. Similarly, E-alkenyl fluorides can be synthesized from simpler compounds or more complex molecules.

SUBMITTER: Nguyen TT 

PROVIDER: S-EPMC5748243 | biostudies-literature | 2016 Apr

REPOSITORIES: biostudies-literature

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Kinetically controlled E-selective catalytic olefin metathesis.

Nguyen Thach T TT   Koh Ming Joo MJ   Shen Xiao X   Romiti Filippo F   Schrock Richard R RR   Hoveyda Amir H AH  

Science (New York, N.Y.) 20160401 6285


A major shortcoming in olefin metathesis, a chemical process that is central to research in several branches of chemistry, is the lack of efficient methods that kinetically favor E isomers in the product distribution. Here we show that kinetically E-selective cross-metathesis reactions may be designed to generate thermodynamically disfavored alkenyl chlorides and fluorides in high yield and with exceptional stereoselectivity. With 1.0 to 5.0 mole % of a molybdenum-based catalyst, which may be de  ...[more]

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