January 3, 2018 Journal article Open Access

Guojiao Wu and Axel Jacobi von Wangelin

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{"conceptdoi":"10.25592/uhhfdm.683","conceptrecid":"683","created":"2019-10-24T13:00:45.231020+00:00","doi":"10.25592/uhhfdm.684","id":684,"links":{"badge":"https://www.fdr.uni-hamburg.de/badge/doi/10.25592/uhhfdm.684.svg","conceptbadge":"https://www.fdr.uni-hamburg.de/badge/doi/10.25592/uhhfdm.683.svg","conceptdoi":"http://doi.org/10.25592/uhhfdm.683","doi":"http://doi.org/10.25592/uhhfdm.684"},"metadata":{"access_right":"open","access_right_category":"success","communities":[{"id":"uhh"}],"creators":[{"name":"Guojiao Wu and Axel Jacobi von Wangelin"}],"description":"<p>Stereoselective additions of highly functionalized reagents to available unsaturated hydrocarbons are an<br>\nattractive synthetic tool due to their high atom economy, modularity, and rapid generation of<br>\ncomplexity. We report efficient cobalt-catalyzed (E)-halofluoroalkylations of alkynes/alkenes that enable<br>\nthe construction of densely functionalized, stereodefined fluorinated hydrocarbons. The mild conditions<br>\n(2 mol% cat., 20 C, acetone/water, 3 h) tolerate various functional groups, i.e. halides, alcohols,<br>\naldehydes, nitriles, esters, and heteroarenes. This reaction is the first example of a highly stereoselective<br>\ncobalt-catalyzed halo-fluoroalkylation. Unlike related cobalt-catalyzed reductive couplings and Hecktype<br>\nreactions, it operates via a radical chain mechanism involving terminal halogen atom transfer which<br>\nobviates the need for a stoichiometric sacrificial reductant.</p>","doi":"10.25592/uhhfdm.684","language":"eng","license":{"id":"CC-BY-4.0"},"publication_date":"2018-01-03","related_identifiers":[{"identifier":"10.25592/uhhfdm.683","relation":"isVersionOf","scheme":"doi"}],"relations":{"version":[{"count":1,"index":0,"is_last":true,"last_child":{"pid_type":"recid","pid_value":"684"},"parent":{"pid_type":"recid","pid_value":"683"}}]},"resource_type":{"subtype":"article","title":"Journal article","type":"publication"},"title":"Stereoselective cobalt-catalyzed halofluoroalkylation of alkynes"},"owners":[35],"revision":2,"updated":"2019-10-24T13:23:49.148348+00:00"}