Manganese-Catalyzed Electrochemical Deconstructive Chlorination of Cycloalkanols via Alkoxy Radicals
A manganese-catalyzed electrochemical deconstructive chlorination of cycloalkanols has been developed. This electrochemical method provides access to alkoxy radicals from alcohols and exhibits a broad substrate scope, with various cyclopropanols and cyclobutanols converted into synthetically useful β- and γ-chlorinated ketones (40 examples). Furthermore, the combination of recirculating flow electrochemistry and continuous inline purification was employed to access products on a gram scale.
Allen, Benjamin D. W.,Hareram, Mishra Deepak,Seastram, Alex C.,McBride, Tom,Wirth, Thomas,Browne, Duncan L.,Morrill, Louis C.
supporting information
p. 9241 - 9246
(2019/11/19)
Tandem decarboxylative allylation and fragmentation of allyl benzocyclobutenyl carbonates: Access to ortho-functionalized aryls from aryl bromides
Allyl benzocyclobutyl carbonates yield ortho-allyl α-aryl ketones through a palladium-catalyzed decarboxylative allylation, fragmentation, and cross-coupling process. Georg Thieme Verlag Stuttgart · New York.
Preparation of benzocyclobutenols by low temperature reaction of ketone enolates with benzynes
The reaction of benzynes, generated from halobenzenes with lithium tetramethylpipiperide (LTMP) at -40 to -78°C, with ketone enolates affords benzocyclobutenols in fair to good yields.
Tripathy, Sasmita,Reddy, Ranga,Durst, Tony
p. 997 - 1002
(2007/10/03)
DECOMPOSITION ACIDO-CATALYSEE D'AZIDES TERTIAIRES BENZOCYCLOBUTENIQUES. NOUVELLE METHODE DE SYNTHESE DU NOYAU INDOLIQUE PAR EXTENSION DU CYCLE
Treatment of benzocyclobutenols substituted on the functional carbon by the HN3/BF3-Et2O reagent allows the synthesis to the corresponding tertiary azides.The latter by acid-catalysed breakdown, lead to 2-substituted indoles.A similar result is obtained by treating directly the alcohols with hydrazoic acid and concentrated sulfuric acid.This new route to indole nucleus is also extended to the synthesis of policyclic indoles.
Adam, G.,Andrieux, J.,Plat, M
p. 399 - 408
(2007/10/02)
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