58463-02-8Relevant academic research and scientific papers
An unprecedented stereoselective titanium-mediated dihydrodimerization of allyl ethers and allylamines
De Meijere, Armin,Stecker, Bj?rn,Kourdioukov, Alexandre,Williams, Craig M.
, p. 929 - 934 (2000)
3-Phenylallyl ether 17, 2,5-dihydrofuran (1) and N-acceptor-substituted 2,5-dihydropyrrols 4, 6, 8, 10, 12 upon treatment with cyclohexylmagnesium bromide in the presence of Ti(Oi-Pr)4 were found to undergo a diastereoselective dihydrodimerization affording 1,5-dienes, d,1-2,3- diethenylbutane-1,4-diol (51% yield) and d,1-2,3-diethenyl-1,4- bis(sulfonylamino)butanes (43-52%), respectively. In the presence of titanium bis(4R,5R)-taddolate, the dihydrodimerization of 1 proceeded with 35-38% chemical yield and up to 94% ee.
A synthesis of allylboronates via the palladium(0)-catalyzed cross-coupling reaction of bis(pinacolato)diboron with allylic acetates
Ishiyama, Tatsuo,Ahiko, Taka-Aki,Miyaura, Norio
, p. 6889 - 6892 (1996)
The cross-coupling reaction of bis(pinacolato)diboron [(Me4C2O2)BB(O2C2Me4)] with allyl acetates regio- and E-stereoselectively provided the pinacol esters of allylboronic acids in high yields. The reaction was efficiently catalyzed by Pd[dba]2 in DMSO at 50°C.
Cobalt-Catalyzed Diastereo- And Enantioselective Reductive Allyl Additions to Aldehydes with Allylic Alcohol Derivatives via Allyl Radical Intermediates
Wang, Lei,Wang, Lifan,Li, Mingxia,Chong, Qinglei,Meng, Fanke
, p. 12755 - 12765 (2021/08/30)
Catalytic generation of ambiphilic π-allyl-metal complexes and their utility in enantioselective transformations constitutes a powerful approach for introduction of allyl groups to a molecule. Herein an unprecedented cobalt-catalyzed highly site-, diastereo-, and enantioselective protocol for stereoselective formation of nucleophilic allyl-Co(II) complexes followed by addition to aldehydes is presented. The reaction features diastereo- and enantioconvergent conversion of easily accessible allylic alcohol derivatives to diversified enantioenriched homoallylic alcohols with a remarkably broad scope of allyl groups that can be introduced. Mechanistic studies indicated that allyl radical intermediates were involved in this process. These new discoveries establish a new strategy for development of enantioselective transformations through capture of radicals by chiral Co complexes, pushing forward the frontier of Co complexes for enantioselective catalysis.
Palladium-Catalyzed Allyl-Allyl Reductive Coupling of Allylamines or Allylic Alcohols with H2as Sole Reductant
Zhou, Xibing,Zhang, Guoying,Huang, Renbin,Huang, Hanmin
, p. 365 - 369 (2021/01/26)
Catalytic carbon-carbon bond formation building on reductive coupling is a powerful method for the preparation of organic compounds. The identification of environmentally benign reductants is key for establishing an efficient reductive coupling reaction. Herein an efficient strategy enabling H2 as the sole reductant for the palladium-catalyzed allyl-allyl reductive coupling reaction is described. A wide range of allylamines and allylic alcohols as well as allylic ethers proceed smoothly to deliver the C-C coupling products under 1 atm of H2. Kinetic studies suggested that the dinuclear palladium species was involved in the catalytic cycle.
Nickel-Catalyzed Homo- And Cross-Coupling of Allyl Alcohols via Allyl Boronates
Gan, Yi,Hu, Hui,Liu, Yuanhong
supporting information, p. 4418 - 4423 (2020/06/27)
A nickel-catalyzed homo- and cross-coupling of allylic alcohols to 1,5-dienes in the presence of B2pin2 with excellent regioselectivity has been developed. Mechanistic studies indicate that the reaction proceeds via sequential nickel-catalyzed borylation of allyl alcohols followed by cross-coupling of the resulting allyl boronates with allyl alcohols. The method was effectively applied to nickel-catalyzed allylation of aldehydes using allylic alcohols directly.
Cobalt-Catalyzed Csp3?Csp3Homocoupling
Cai, Yingxiao,Qian, Xin,Gosmini, Corinne
supporting information, p. 2427 - 2430 (2016/08/16)
An efficient and easy method for Csp3?Csp3homocoupling was developed using cobalt bromide as catalyst. A series of functionalized alkyl bromides and alkyl chlorides were coupled in high yields under mild conditions. This reaction seems to involve a radical intermediate. (Figure presented.).
Copper-catalysed α-selective allylic alkylation of heteroaryllithium reagents
Vila, Carlos,Hornillos, Valentn,Faans-Mastral, Martn,Feringa, Ben L.
, p. 9321 - 9323 (2014/12/11)
2-Allyl-substituted thiophenes and furans are synthesised efficiently in a direct procedure using 2-heteroaryllithium reagents and allyl bromides and chlorides catalysed by ligand-free copper(i). The reactions take place under mild conditions, with excellent α-selectivity, high functional group tolerance and good yields for the SN2 products. This journal is
Single electron transfer-induced Grignard cross-coupling involving ion radicals as exclusive intermediates
Uchiyama, Nanase,Shirakawa, Eiji,Hayashi, Tamio
supporting information, p. 364 - 366 (2013/02/23)
The mechanism of the previously developed cross-coupling reaction of aryl Grignard reagents with aryl halides was explored in more detail. Single electron transfer from an aryl Grignard reagent to an aryl halide initiates a radical chain by giving an anion radical of the aryl halide. The following propagation cycle consists entirely of anion radical intermediates.
Selective cross-coupling of organic halides with allylic acetates
Anka-Lufford, Lukiana L.,Prinsell, Michael R.,Weix, Daniel J.
, p. 9989 - 10000 (2013/01/15)
A general protocol for the coupling of haloarenes with a variety of allylic acetates is presented. Strengths of the method are a tolerance for electrophilic (ketone, aldehyde) and acidic (sulfonamide, trifluoroacetamide) substrates and the ability to couple with a variety of substituted allylic acetates. Secondary alkyl bromides can also be allylated under slightly modified conditions, demonstrating the generality of the approach. Finally, the coupling of a reactive vinyl halide could be achieved by the use of a very hindered ligand and more reactive, branched allylic acetates.
Nickel-catalyzed, sodium iodide-promoted reductive dimerization of alkyl halides, alkyl pseudohalides, and allylic acetates
Prinsell, Michael R.,Everson, Daniel A.,Weix, Daniel J.
supporting information; experimental part, p. 5743 - 5745 (2010/09/18)
The first general method for the reductive dimerization of alkyl halides, alkyl mesylates, alkyl trifluoroacetates, and allylic acetates is reported which proceeds with low catalyst loading (0.5 to 5 mol%), generally high yields (80% ave yield), and good functional-group tolerance.
