Preparation of Imides via the Palladium-Catalyzed Coupling Reaction of Organoborons with Methyl <i>N</i>-[Methoxy(methylthio)methylene]carbamate as a One-Carbon Elongation Reaction

Tomizawa, Takuhei; Orimoto, Kohei; Niwa, Takashi; Nakada, Masahisa

doi:10.1021/ol303062a

Cited by 23 publications

(12 citation statements)

References 28 publications

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“…The multiple carbon insertion into a C-B bond was observed as follows. A trialkylborane, 9-(2-phenethyl)-BBN, prepared by hydroboration of styrene with 9-H-BBN, 21 was allowed to react with CO in the presence and absence of hydride reagents. After subsequent oxidative workup with hydrogen peroxide in a pH 7 buffer, the product mixture was analyzed by GC, GC-MS and 1 H NMR spectroscopy.…”

Section: Scheme 1 Formation Of Methylene Linkers From Co In the Absence Of Heavy Metalsmentioning

confidence: 99%

Heavy-Metal-Free Fischer–Tropsch Type Reaction: Sequential Homologation of Alkylborane Using a Combination of CO and Hydrides as Methylene Source

et al. 2020

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Carbon homologation reactions occur within the well-known Fischer-Tropsch process, usually mediated by transition metal catalysts at high temperature. Here we report the low-temperature, heavy metal-free homologation of a carbon chain using CO as a C1-source showing for the first time that transition-metal catalysts are not required for Fischer-Tropsch-type reactivity. Reaction of an alkylborane in the presence of either LiHBEt3 or LiAlH4 resulted in multiple CO insertion/reduction events to afford elongated chains by more than two methylene (-CH2-) units, affording aldehyde products upon oxidative aqueous work-up. Theoretical and experimental mechanistic studies indicate that the boron-terminus is responsible for CO incorporation as well as sequential hydride delivery leading to reduction of acylborane intermediates to alkylboranes.

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Section: Scheme 1 Formation Of Methylene Linkers From Co In the Absence Of Heavy Metalsmentioning

confidence: 99%

Heavy-Metal-Free Fischer–Tropsch Type Reaction: Sequential Homologation of Alkylborane Using a Combination of CO and Hydrides as Methylene Source

et al. 2020

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“…In 2012, Nakada and co‐workers reported an efficient Liebeskind–Srogl‐type cross‐coupling reaction between N ‐[methoxy(methylthio)methylene]carbamate ( 117 ) and aryl‐, alkenyl‐, or alkylboron reagents (Scheme ) . Notably, the resultant iminoethers ( 118 ) could either be isolated or converted into imides 119 or esters 120 through hydrolysis or alcoholysis, respectively, in good‐to‐excellent yields.…”

Section: Pd‐catalyzed Liebeskind–srogl Cross‐ Coupling Reactions (Fimentioning

confidence: 99%

The Liebeskind–Srogl Cross‐Coupling Reaction and its Synthetic Applications

et al. 2018

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The Pd-catalyzed, Cu I Àcarboxylate-mediated crosscoupling reactiono fo rganosulfur compounds with nucleophilic organometallic reagents is knowna st he Liebeskind-Srogl cross-coupling reaction. Owing to the readily available starting materials and neutral reactionc onditions, it has become an attractive procedure for the formation of carbonÀcarbon bonds, in particularf or cases in whicht radi-tional methods had failed. Since the seminal work of Liebeskind and Srogl in 2000, this reactionh as received intense attentionf rom the synthetic community.I nt his Focus Review,w eh ighlight recent advances in this intriguing cross-coupling reactiona nd its applications in organic synthesis.Scheme1.Liebeskind-Srogl cross-coupling reaction.Scheme2.The original Liebeskind-Sroglc ross-coupling reaction.d ba = dibenzylideneacetone, TFP = tri-2-furanylphosphine [a] Dr.Scheme4.Cross-coupling reaction between a-amino acid thiol esters and organostannanes. Cbz = benzyloxycarbonyl.Scheme5.Cross-coupling reaction between thiol esters and B-alkyl-9-BBN. 9-BBN = 9-borabicyclo[3.3.1]nonane.Scheme6.One-pothydroboration/intramolecular-cross-couplingr eaction between thiol esters and B-alkyl-9-BBN. DIPEA = N,N-diisopropylethylamine.Scheme7.Cross-coupling reaction between thiol esters andorganoindium reagents.Scheme8.Cross-coupling reaction between thiol esters andorganosilicon reagents. TBAF = tetra-n-butylammonium fluoride.Scheme9.Intramolecular cross-coupling reaction between thiol esters and olefins.Scheme38. Cross-coupling reaction between diaryld isulfides and boronicacids/terminal-alkynes.Scheme55. Synthesis of the C 15 ÀC 36 segment of goniodomin A. TBS = tert-butyldimethylsilyl, TBDPS = tert-butyldiphenylsilyl.Scheme56. To talsynthesis of verbenachalcone. MOM = methoxymethyl.Scheme57. Synthesis of enigmol and its stereoisomers. Boc = tert-butyloxycarbonyl.Scheme58. To talsynthesis of (À)-agelastatins A-F.Scheme59. Synthesis of quinone-containing salvinorin Aa nalogues.Scheme60. Synthesis of Soai-type aldehydes.

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“…The reaction afforded imino ethers that were easily converted to the corresponding imides by acidic hydrolysis in high yield. ( Scheme 13 ) [ 52 ].…”

Section: Suzuki-miyaura Coupling Of Acyl Chlorides and Anhydridesmentioning

confidence: 99%

Suzuki-Miyaura Cross-Coupling in Acylation Reactions, Scope and Recent Developments

et al. 2013

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Since the first report and due to its handiness and wide scope, the Suzuki-Miyaura (SM) cross coupling reaction has become a routine methodology in many laboratories worldwide. With respect to other common transition metal catalyzed cross couplings, the SM reaction has been so far less exploited as a tool to introduce an acyl function into a specific substrate. In this review, the various approaches found in the literature will be considered, starting from the direct SM acylative coupling to the recent developments of cross coupling between boronates and acyl chlorides or anhydrides. Special attention will be dedicated to the use of masked acyl boronates, alkoxy styryl and alkoxy dienyl boronates as coupling partners. A final section will be then focused on the acyl SM reaction as key synthetic step in the framework of natural products synthesis.

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Preparation of Imides via the Palladium-Catalyzed Coupling Reaction of Organoborons with Methyl N-[Methoxy(methylthio)methylene]carbamate as a One-Carbon Elongation Reaction

Cited by 23 publications

References 28 publications

Heavy-Metal-Free Fischer–Tropsch Type Reaction: Sequential Homologation of Alkylborane Using a Combination of CO and Hydrides as Methylene Source

Heavy-Metal-Free Fischer–Tropsch Type Reaction: Sequential Homologation of Alkylborane Using a Combination of CO and Hydrides as Methylene Source

The Liebeskind–Srogl Cross‐Coupling Reaction and its Synthetic Applications

Suzuki-Miyaura Cross-Coupling in Acylation Reactions, Scope and Recent Developments

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