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Arjun Gontala,Gwang Seok Jang,Sang Kook Woo 대한화학회 2021 Bulletin of the Korean Chemical Society Vol.42 No.3
The development of a greener allylation reagent for α-allylation of carbonyl compounds is of great necessity. Here we present allyltrimethylsilane as a novel allylation reagent in the photoredox-catalyzed α-allylation of carbonyl compounds such as ketones, esters, and amides. The reaction process shows good functional group tolerance and generates a good yield of the product. The reaction mechanism is a radical-mediated reaction by photo-induced single electron transfer.
Seomoon, Dong,Lee, Kooyeon,Kim, Hyunseok,Lee, Phil ,Ho Wiley - VCH Verlag GmbH & Co. KGaA 2007 Chemistry Vol.13 No.18
<P>Inter- and intramolecular palladium-catalyzed allyl cross-coupling reactions using allylindium generated in situ by treatment of allyl acetates with indium and indium trichloride in the presence of Pd<SUP>0</SUP> catalyst and nBuNMe<SUB>2</SUB> in DMF were successfully demonstrated. Allylindium species generated in situ by reductive transmetalation of π-allylpalladium(II) complexes, obtained from a variety of allyl acetates in the presence of Pd<SUP>0</SUP> catalyst together with indium and indium trichloride, were found to be capable of acting as effective nucleophilic coupling partners in Pd-catalyzed cross-coupling reactions. A variety of allyl acetates such as but-1-en-3-yl acetate, crotyl acetate, and 2-methylallyl acetate afforded the corresponding allylic compounds in good yields in cross-coupling reactions. Various electrophilic cross-coupling partners such as aryl iodides and vinyl bromides and triflates participate in these reactions. Not only intermolecular but also intramolecular Pd-catalyzed cross-coupling reactions work equally well to produce the desired allylic coupling products in good yields.</P> <B>Graphic Abstract</B> <P>Inter- and intramolecular cross-coupling reactions work equally well: Allylindium species generated in situ by reductive transmetalation of π-allylpalladium(II) complexes, obtained from a variety of allyl acetates in the presence of a Pd<SUP>0</SUP> catalyst together with indium and indium trichloride, were found to be capable of acting as effective nucleophilic coupling partners in intermolecular and intramolecular Pd-catalyzed cross-coupling reactions. <img src='wiley_img/09476539-2007-13-18-CHEM200601338-content.gif' alt='wiley_img/09476539-2007-13-18-CHEM200601338-content'> </P>
Jo, H.,Han, S.,Park, J.,Choi, M.,Han, S.H.,Jeong, T.,Lee, S.Y.,Kwak, J.H.,Jung, Y.H.,Kim, I.S. Pergamon Press 2016 Tetrahedron Vol.72 No.4
<P>The rhodium(III)-catalyzed mild and site-selective C-H allylation of 2-arylbenzo[d]thiazoles and 2-arylbenzo[d]oxazoles with allylic phosphonates and allylic carbonates is described. This transformation provides an efficient construction of C2-allylated, crotylated and prenylated 2-arylbenzo[d] thiazoles and 2-arylbenzo[d]oxazoles. In addition, this protocol can be applied to the formation of 2-arylbenzo[d]thiazole scaffolds containing an allylic alcohol group by using of 4-vinyl-1,3-dioxolan-2-one and vinyl oxirane as coupling partners. (C) 2015 Elsevier Ltd. All rights reserved.</P>
Yu, Chan-Mo,Youn, Jin-soup,Jung, Hee-Keum Korean Chemical Society 2006 Bulletin of the Korean Chemical Society Vol.27 No.4
The preparation of enatiomerically enriched homoallylic alcohols through asymmetric addition of chiral allylic transfer reagents and allylating reagents with chiral catalysts to the carbonyl functionalities represents an important chemical transformation. Excellent progress has been made over past decade in the development and application of catalytic asymmetric allylic transfer reactions. In this account, our efforts for the various intermolecular allylic transfer reactions such as allylation, propargylation, allenylation, and dienylation utilizing accelerating strategy and sequential allylic transfer reactions to achieve multiple stereoselection mainly using transition metal catalysts are described.
Rambabu N. Reddi,Changbum Jo,Arumugam Sudalai 대한화학회 2022 Bulletin of the Korean Chemical Society Vol.43 No.10
This article describes a concise synthesis of two important fragments (tetrahydropyran [THP] and ketone moieties) of the cytotoxic macrolide (+)-neopeltolide in 10 long linear steps in enantiomerically pure form. Asymmetric Keck allylation to install the required C11 and C13 stereocenters, N-heterocyclic carbene (NHC)-catalyzed oxoacyloxylation to functionalize alkenes, and reductive oxa-Michael addition to construct 2,6-difunctionalized THP unit intramolecularly are the important steps in synthetic efforts. Finally, Keck asymmetric allylation and Lewis acid-catalyzed diastereoselective allylation of the aldehyde were sequentially employed to establish the stereocenters at C11 and C13 positions, respectively.
Phil Ho Lee*,Eunkyong Shim,이구연,Dong Seomoon,Sundae Kim 대한화학회 2005 Bulletin of the Korean Chemical Society Vol.26 No.1
Allylindium and propargylindium reagents in situ generated from the reactions of indium with allyl halides and propargyl halides could participate as nucleophiles in Pd-catalyzed substitution reactions of allyl carbonates to produce 1,5-dienes and 1,5-enynes in good yields. β-Hydride elimination products were produced in case of carbonates having β-hydrogens. Because organoindium reagents obtained from allyl or propargyl halides and indium have previously not been used to Pd-catalyzed allylic and propargylic substitution reactions, these results should provide more opportunities for the development of new C-C bond forming reactions.
Facile Direct Coupling Reactions of MOM-protected Benzylic Alcohols Using Aluminum Chloride
Bui Tien Tan,Kim Hee‐Kwon 대한화학회 2021 Bulletin of the Korean Chemical Society Vol.42 No.9
MOM group is one of the most commonly used protecting groups for alcohols. This study describes novel direct functionalization of the MOM-protected benzylic alcohols. Preparation of allylic compounds from benzyl MOM ethers was successfully achieved by utilization of allyltrimethylsilane and AlCl3. In addition, direct azidation of benzyl MOM ethers using TMSN3 was successful carried out under AlCl3- mediated reaction conditions. These results demonstrate that this novel synthetic procedure is a promising approach to direct functionalization of MOM-protected alcohols including allylation and azidation.
Seok Won Kang,Eun Young Heo,전종갑,Sung Hoon Kim 대한화학회 2004 Bulletin of the Korean Chemical Society Vol.25 No.12
Allylations of N-benzyl and N-methyl cyclic imides were accomplished successfully under mild Barbier type conditions using zinc metal, allyl bromide and catalytic amount of PbBr2. Subsequent coupling reactions with some carbon nucleophiles afforded 1,2- and 1,4-addition products in moderate to high yields.
Synthesis of ($\pm$)-Methyl-(1-aryl-4-pyridin-3-yl-but-3-enyl)-amines
Jang, Jin-Hee,Sin, Kwan-Seog,Park, Hae-Il The Pharmaceutical Society of Korea 2001 Archives of Pharmacal Research Vol.24 No.6
trans-Metanicotine, a subtype (${\alpha}_4{\beta}_2$)-selective ligand for neuronal nicotinic acetylcholine receptor, is under clinical phase for Alzheimer's disease. An efficient synthetic route for ($\pm$)-methyl-(1-aryl-4-pyridin-3-yl-but-3-enyl)-am ices, derivatives of tracts-metanicotine, was explored. Allylation reaction of aryl aldimines with allylmagnesium bromide in THF gave ($\pm$)-methyl-(1-aryl-but-3-enyl)-amines. Protection of the amines with the Boc group and following Heck reaction of the N-Boc amines with 3-bromopyridine gave ($\pm$)-methyl-(1-aryl-4-pyridin-3-yl-but-3-enyl)-carbamic acid tert-butyl esters. Deprotection of the N-Boc group in aqueous 1 N-HCI solution gave the titled amines in good yields. Thus, trans-metanicotine analogues modified at the ${\alpha}-position$ of the methylamino group with amyl groups were obtained in 5 steps.
Kang, Seok-Won,Heo, Eun-Young,Jun, Jong-Gab,Kim, Sung-Hoon Korean Chemical Society 2004 Bulletin of the Korean Chemical Society Vol.25 No.12
Allylations of N-benzyl and N-methyl cyclic imides were accomplished successfully under mild Barbier type conditions using zinc metal, allyl bromide and catalytic amount of $PbBr_2$. Subsequent coupling reactions with some carbon nucleophiles afforded 1,2- and 1,4-addition products in moderate to high yields.