80203-35-6Relevant academic research and scientific papers
Contra-thermodynamic Olefin Isomerization by Chain-Walking Hydroboration and Dehydroboration
Bloomer, Brandon,Butcher, Trevor W.,Ciccia, Nicodemo R.,Conk, Richard J.,Hanna, Steven,Hartwig, John F.
, p. 1005 - 1010 (2022/02/10)
We report a dehydroboration process that can be coupled with chain-walking hydroboration to create a one-pot, contra-thermodynamic, short-or long-range isomerization of internal olefins to terminal olefins. This dehydroboration occurs by a sequence comprising activation with a nucleophile, iodination, and base-promoted elimination. The isomerization proceeds at room temperature without the need for a fluoride base, and the substrate scope of this isomerization is expanded over those of previous isomerizations we have reported with silanes.
Copper-Catalyzed Alkoxycarbonylation of Alkyl Iodides for the Synthesis of Aliphatic Esters: Hydrogen Makes the Difference
Geng, Hui-Qing,Wu, Xiao-Feng
supporting information, p. 8062 - 8066 (2021/10/25)
A copper-catalyzed alkoxycarbonylation transformation of unactivated alkyl iodides has been developed. Various alkyl iodides can be converted into the corresponding tert-butyl esters in good yields. NaOtBu acts as both a nucleophile and a base. Moreover, other types of aliphatic esters can also be obtained in moderated yields if extra alcohols are added. Both primary and secondary alkyl alcohols can react successfully.
Copper-Catalyzed Regioselective Borocarbonylative Coupling of Unactivated Alkenes with Alkyl Halides: Synthesis of β-Boryl Ketones
Wu, Fu-Peng,Yuan, Yang,Schünemann, Claas,Kamer, Paul C. J.,Wu, Xiao-Feng
supporting information, p. 10451 - 10455 (2020/05/08)
The borocarbonylative coupling of unactivated alkenes with alkyl halides remains a challenge. In this communication, a Cu-catalyzed borocarbonylative coupling of unactivated alkenes with alkyl halides for the synthesis of β-boryl ketones has been developed. A broad range of β-boryl ketone derivatives was prepared in moderate to excellent yields with complete regioselectivity.
Transition-Metal-Free Borylation of Alkyl Iodides via a Radical Mechanism
Liu, Qianyi,Hong, Junting,Sun, Beiqi,Bai, Guangcan,Li, Feng,Liu, Guoquan,Yang, Yang,Mo, Fanyang
supporting information, (2019/07/08)
We describe an operationally simple transition-metal-free borylation of alkyl iodides. This method uses commercially available diboron reagents as the boron source and exhibits excellent functional group compatibility. Furthermore, a diverse range of prim
Electrophilic Iron Catalyst Paired with a Lithium Cation Enables Selective Functionalization of Non-Activated Aliphatic C?H Bonds via Metallocarbene Intermediates
Hernán-Gómez, Alberto,Rodríguez, Mònica,Parella, Teodor,Costas, Miquel
supporting information, p. 13904 - 13911 (2019/08/30)
Combining an electrophilic iron complex [Fe(Fpda)(THF)]2 (3) [Fpda=N,N′-bis(pentafluorophenyl)-o-phenylenediamide] with the pre-activation of α-alkyl-substituted α-diazoesters reagents by LiAl(ORF)4 [ORF=(OC(CF3)3] provides unprecedented access to selective iron-catalyzed intramolecular functionalization of strong alkyl C(sp3)?H bonds. Reactions occur at 25 °C via α-alkyl-metallocarbene intermediates, and with activity/selectivity levels similar to those of rhodium carboxylate catalysts. Mechanistic investigations reveal a crucial role of the lithium cation in the rate-determining formation of the electrophilic iron-carbene intermediate, which then proceeds by concerted insertion into the C?H bond.
Visible-Light-Promoted Remote C-H Functionalization of o-Diazoniaphenyl Alkyl Sulfones
Du, Shaofu,Kimball, Elizabeth Ann,Ragains, Justin R.
supporting information, p. 5553 - 5556 (2017/10/25)
Visible-light irradiation of ortho-diazoniaphenyl alkyl sulfones in the presence of Ru(bpy)32+ results in remote Csp3-H functionalization. Key mechanistic steps in these processes involve intramolecular hydrogen atom transfer from Csp3-H bonds to aryl radicals to generate alkyl/benzyl radicals. Subsequent polar crossover occurs by single-electron oxidation of the alkyl/benzyl radicals to carbenium ions that then intercept nucleophiles. We have developed remote hydroxylations, etherifications, an amidation, and C-C bond formation processes using this strategy.
One-Pot Transformation of Aliphatic Carboxylic Acids into N-Alkylsuccin-imides with NIS and NCS/NaI
Nakai, Yuhta,Moriyama, Katsuhiko,Togo, Hideo
, p. 768 - 772 (2017/01/18)
Primary aliphatic carboxylic acids were treated with N-iodosuccinimide (NIS) in 1,2-dichloroethane to form the corresponding alkyl iodides under warming conditions. Based on these results, those aliphatic carboxylic acids were treated with NIS, followed by the reaction with K2CO3to give the corresponding N-alkylsuccinimides in good yields in one pot. Moreover, those aliphatic carboxylic acids were treated with N-chlorosuccinimide (NCS) and NaI, followed by the reaction with K2CO3to provide the corresponding N-alkylsuccinimides in good to moderate yields in one pot. By using the present method, successive treatment of primary aliphatic carboxylic acids (10 mmol) with NIS, K2CO3, and then hydrazine provided the corresponding decarboxylated primary amines in good yield.
ACC INHIBITORS AND USES THEREOF
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Paragraph 0687; 0688; 0689, (2013/05/22)
The present invention provides compounds useful as inhibitors of Acetyl CoA Carboxylase (ACC), compositions thereof, and methods of using the same.
PROCESS FOR THE PREPARATION OF IODIDES
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Page/Page column 29, (2012/01/05)
This invention is directed to a process for the preparation of high yield alkyl or aryl iodide from its corresponding carboxylic acid using N-iodo amides.
Metal-free efficient, general and facile iododecarboxylation method with biodegradable co-products
Kulbitski, Kseniya,Nisnevich, Gennady,Gandelman, Mark
supporting information; experimental part, p. 1438 - 1442 (2011/07/30)
The development of a novel, efficient and robust method for the general conversion of aliphatic and aromatic carboxylic acids to organic iodides without the use of heavy metals or strong oxidizing agents is reported. Commercially available N-iodoamides were used for both initiation and halogen donation under irradiative conditions. Isolation of the product is extremely simple and the major co-product is removed as a water-soluble biodegradable material. Copyright
