34008-71-4Relevant articles and documents
Additive-Free Isomerization of Allylic Alcohols to Ketones with a Cobalt PNP Pincer Catalyst
Spiegelberg, Brian,Dell'Acqua, Andrea,Xia, Tian,Spannenberg, Anke,Tin, Sergey,Hinze, Sandra,de Vries, Johannes G.
supporting information, p. 7820 - 7825 (2019/05/22)
Catalytic isomerization of allylic alcohols in ethanol as a green solvent was achieved by using air and moisture stable cobalt (II) complexes in the absence of any additives. Under mild conditions, the cobalt PNP pincer complex substituted with phenyl groups on the phosphorus atoms appeared to be the most active. High rates were obtained at 120 °C, even though the addition of one equivalent of base increases the speed of the reaction drastically. Although some evidence was obtained supporting a dehydrogenation–hydrogenation mechanism, it was proven that this is not the major mechanism. Instead, the cobalt hydride complex formed by dehydrogenation of ethanol is capable of double-bond isomerization through alkene insertion–elimination.
Cu-catalyzed sequential dehydrogenation-conjugate addition for β-functionalization of saturated ketones: Scope and mechanism
Jie, Xiaoming,Shang, Yaping,Zhang, Xiaofeng,Su, Weiping
supporting information, p. 5623 - 5633 (2016/05/24)
The first copper-catalyzed direct β-functionalization of saturated ketones is reported. This protocol enables diverse ketones to couple with a wide range of nitrogen, oxygen and carbon nucleophiles in generally good yields under operationally simple conditions. The detailed mechanistic studies including kinetic studies, KIE measurements, identification of reaction intermediates, EPR and UV-visible experiments were conducted, which reveal that this reaction proceeds via a novel radical-based dehydrogenation to enone and subsequent conjugate addition sequence.
Oxa-Michael addition promoted by the aqueous sodium carbonate
Guo, Shi-Huan,Xing, Sheng-Zhu,Mao, Shuai,Gao, Ya-Ru,Chen, Wen-Liang,Wang, Yong-Qiang
, p. 6718 - 6720 (2014/12/11)
An efficient Michael addition of alcohols to activated alkenes promoted by sodium carbonate with water as reaction medium has been developed. The reaction provides a general, economical and environmentally friendly approach for the synthesis of β-alkoxycarbonyl compounds.
Unveiling the reactivity of propargylic hydroperoxides under gold catalysis
Alcaide, Benito,Almendros, Pedro,Quiros, M. Teresa,Lopez, Ramon,Menendez, Maria I.,Sochacka-Cwikla, Aleksandra
, p. 898 - 905 (2013/03/14)
Controlled gold-catalyzed reactions of primary and secondary propargylic hydroperoxides with a variety of nucleophiles including alcohols, phenols, 2-hydroxynaphthalene-1,4-dione, and indoles allow the direct and efficient synthesis of β-functionalized ke
Platinum-catalyzed multi-step reaction of propargyl alcohols with N-heteroaromatics
Bhuvaneswari, Sivakolundu,Jeganmohan, Masilamani,Cheng, Chien-Hong
experimental part, p. 141 - 146 (2010/04/23)
N-Methyl indole reacts with but-2-yn-1-ol in the presence of PtCl 2 in MeOH giving indole derivatives having a substituted 3-oxobutyl group at the 3-position in good yield. Under the reaction conditions, various substituted indoles and substituted propargyl alcohols are successfully involved in the reaction giving the corresponding addition products in good to moderate yields. The catalytic reaction can be further extended to N-phenyl pyrrole. In the present multi-step reaction, PtCl2 likely plays dual roles: as the catalyst for the rearrangement of proparg-yl alcohols to the corresponding alken-yl ketones and as the catalyst for the addition of indoles to the alkenyl ke-tones. Experimental evidence is provided to support the proposed mechanism.
Rhodium-catalyzed addition of alcohols to terminal enones
Farnworth, Marc V.,Cross, Michael J.,Louie, Janis
, p. 7441 - 7443 (2007/10/03)
[Rh(COD)(OMe)]2 was found to catalyze the addition of aliphatic and aromatic alcohols with terminal enones to afford β-alkoxyketones in high yields.
Synthesis and Muscarinic Cholinergic Receptor Affinities of 3-Quinuclidinyl α-(Alkoxyalkyl)-α-aryl-α-hydroxyacetates
Cohen, Victor I.,Gibson, Raymond E.,Fan, Linda H.,Cruz, Rosanna De La,Gitler, Miriam S.,et al.
, p. 2989 - 2993 (2007/10/02)
Seven analogues of 3-quinuclidinyl benzilate (QNB) in which one phenyl ring was replaced by an alkoxyalkyl moiety were synthesized and their affinities for the muscarinic cholinergic receptor determined.An oxygen in the β-position of the moienty was not w
Palladium(II)-catalyzed Alkoxylation and Acetoxylation of Alkenes
Hosokawa, Takahiro,Shinohara, Toru,Ooka, Yoshiharu,Murahashi, Shun-Ichi
, p. 2001 - 2004 (2007/10/02)
Addition of alcohols or acetic acid to alkenes activated by carbonyl or acetal is catalyzed by PdCl2(MeCN)2 to give the corresponding ethers and esters.
CATALYTIC REACTION OF 3-PHENYL-2-PROPYN-1-OL WITH ALCOHOLS
Grigorian, S. G.,Avetisyan, K. G.,Matnishyan, A. A.
, p. 1428 - 1430 (2007/10/02)
The cyclic ketal 2,5-dimethyl-2,5-bis(3-phenyl-2-propynyloxy)-1,4-dioxane was obtained by the reaction of 3-phenyl-2-propyn-1-ol with propargyl alcohol in the presence of the HgO-BF3*O(C2H5)2 catalytic system.The transformation of 3-phenyl-2-propyn-1-ol and its ethers in methanol and ethanol by the action of the above-mentioned catalytic system leads to 1-phenyl-3-alkoxy-1-propanone, 1-phenyl-1,1,3-trialkoxypropane, and 1-phenyl-2-propen-1-one.The intermediate organomercury compound, which is the product from regioselective addition of mercuric oxide and the saturatedalcohol at the triple bond, was isolated.Its protodemercuration led to the above-mentioned linear products.The formation of the cyclic ketal is presumably due to the preferred formation of mercury bis-hydroxypropargylide.x
3-Metallated Enamines VI. Use as β-Oxo Vinyl Anion Equivalents
Sudheendranath, C. S.,Ahlbrecht, H.
, p. 973 - 979 (2007/10/02)
Two possibilities to produce a synthetic equivalent for the β-oxo vinyl anion starting from a saturated carbonyl compound are investigated.In the first method, a methylthio group is introduced into the 3-position of the corresponding enamine.Metallation, regioselective attack by an electrophile followed by hydrolysis and oxidative elimination of the methylthio group completes the sequence.In the second method, the trimethyl silyl group is introduced instead.After deprotonation and regioselective reaction with an electrophile, the silylated enamine is chlorinated with N-chloro-succinimid.Dechlorosilylation and simultaneous hydrolysis of the enamine are achieved by means of trifluoro acetic acid/ hydrochloric acid and sodium fluoride in ethanol.
