4885-09-0Relevant articles and documents
Formal metal-free γ-arylation of 1,3-dicarbonyl compounds: Via an isomerisation/1,4-addition/[3,3]-sigmatropic rearrangement sequence
Guan, Xi-Dong,Lu, Shi-Chao,Wen, Fu-Qiang
supporting information, p. 8964 - 8968 (2021/11/27)
A metal-free redox arylation of alkynes with sulfoxides has been developed to provide unconventional access to diverse γ-arylated 1,3-dicarbonyl compounds in an atom-economical manner. Mechanistic studies suggest that a conjugated allenone intermediate was generated in situ, which solves the problem of reactivity and regioselectivity of unsymmetrical dialkyl-substituted internal alkynes and enables the functionalisation of a broad range of substrates bearing electron-withdrawing functional groups. The resulting arylated 1,3-dicarbonyl compounds are versatile and useful building blocks for further functionalisation. This journal is
A method for accessing sulfanylfurans from homopropargylic alcohols and sulfonyl hydrazides
Yan, Rulong,Yang, Xiaodong
supporting information, p. 3571 - 3574 (2019/06/13)
A sulfenylation/cyclization reaction has been developed for the synthesis of sulfanylfurans in the presence of iodine. These processes provide facile strategies to construct C-S/O bonds, and expand the methods of synthesizing sulfanylfurans. In this trans
Regioselective access to CF3S-substituted dihydrofurans from homopropargylic alcohols with trifluoromethanesulfenamide
Chen, Dao-Qian,Gao, Pin,Zhou, Ping-Xin,Song, Xian-Rong,Qiu, Yi-Feng,Liu, Xue-Yuan,Liang, Yong-Min
supporting information, p. 6637 - 6639 (2015/04/14)
A facile access to 4-((trifluoromethyl)thio)-2,3-dihydrofurans from unprotected homopropargylic alcohols in high regioselectivity is reported. This method is the first example of using a free hydroxy group as a nucleophile to complete a trifluoromethylthiolation/cyclization protocol with an alkyne in moderate to excellent yields. This journal is
Ethylene transposition: Ruthenium hydride catalyzed intramolecular trans -silylvinylation of internal alkynes
Liu, Shasha,Zhao, Jinbo,Kaminsky, Lauren,Wilson, Robert J.,Marino, Nadia,Clark, Daniel A.
supporting information, p. 4456 - 4459 (2015/01/16)
A highly selective intramolecular trans-silylvinylation of internal alkynes catalyzed by RuHCl(CO)(SIMes)(PPh3) has been accomplished. The use of methyl vinyl ketone as an additive increased the efficiency of this transformation. This process w
Ring opening/fragmentation of dihydropyrones for the synthesis of homopropargyl alcohols
Tummatorn, Jumreang,Dudley, Gregory B.
, p. 5050 - 5051 (2008/10/09)
Ring-opening/C-C bond cleavage reactions induced by nucleophilic addition of methyl Grignard to 5,6-dihydro-2-pyrone (DHP) triflates 1 furnish homopropargyl alcohols (1 → 2) stereospecifically with respect to the stereochemistry of 1. Carbonyl extrusion from DHP triflates provides a unified and operationally simple strategy for preparing chiral homopropargyl alcohols. Copyright
Regioselective addition reactions of propargyl bromides to carbonyl compounds with gallium catalyzed by indium
Lee, Phil Ho,Kim, Hyun,Lee, Kooyeon
, p. 1219 - 1222 (2007/10/03)
Reactions of organogallium reagents generated from propargyl bromides having substituents at the γ-position and gallium in the presence of 5 mol % of indium with aldehydes and ketones selectively produced homoallenyl alcohols in good to excellent yields.
Intramolecular Substitution Reaction of Lithium Alkylidene Carbenoids. Regioselective Synthesis of Indenes
Yanagisawa, Hideyuki,Miura, Kasei,Kitamura, Mitsuru,Narasaka, Koichi,Ando, Kaori
, p. 2009 - 2026 (2007/10/03)
When 4,4-dibromo-3-alkenols are treated with butyllithium, an intramolecular substitution reaction with alkoxide moiety occurs at the lithium alkylidene carbenoid center to give dihydrofurans. The reaction mechanism of this intramolecular substitution reaction is studied by B3LYP density functional calculations with the 6-31+G(d) basis set, and the substitution is found to proceed in a concerted manner. This substitution reaction is applied to the regioselective preparation of indene derivatives. That is, treatment of 3-(o-bromophenyl)-1,1-dibromopropene derivatives 23 with butyllithium results in the formation of intramolecular substitution intermediates, 3-indenyllithiums D, which are trapped with electrophiles to afford substituted indenes regioselectively.
Carbonyl allenylations and propargylations by 3-chloro-1-propyne or 2-propynyl mesylates with tin(IV) chloride and tetrabutylammonium iodide
Masuyama, Yoshiro,Watabe, Akiko,Kurusu, Yasuhiko
, p. 1713 - 1715 (2007/10/03)
By the use of tin(IV) chloride and tetrabutylammonium iodide in dichloromethane, 3-chloro-1-propyne or 2-propynyl mesylate can be applied to allenylation and propargylation of aldehydes (carbonyl allenylation and propargylation) to produce a mixture of 1-
A highly atom efficient, solvent promoted addition of tetraallylic, tetraallenic, and tetrapropargylic stannanes to carbonyl compounds
McCluskey,Muderawan,Muntari,Young
, p. 7811 - 7817 (2007/10/03)
Tetraallylic, tetraallenic, and tetrapropargylic stannanes (0.25 equiv) react with aldehydes in methanol to provide unsaturated alcohols in good to excellent yields (56-99%). These reactions proceed exclusively with allylic rearrangement for tetra(2-butenyl)tin 2b and tetra(1,2-butadienyl)-tin 16c and predominantly with allylic rearrangement for tetrapropadienyltin 16a and tetra(2-butynyl)tin 6e. Allylation reactions also proceeded smoothly with reactive ketones such as ethyl pyruvate (9a) and cyclohexanone (9b). The corresponding TFA-catalyzed reactions of dimethyl acetals 4d and 4e are regiospecific with allylic rearrangement.
Indium mediated allylation and propargylation reactions of dimethyl acetals and ketals
Kwon, Jin Sun,Pae, Ae Nim,Choi, Kyung Il,Koh, Hun Yeong,Kim, Youseung,Cho, Yong Seo
, p. 1957 - 1959 (2007/10/03)
Indium mediated allylation and propargylation reactions of acetals and ketals with various allyl or propargyl bromides in aqueous media successfully provided the corresponding homoallylic or homopropargylic (and allenylic) alcohol, respectively, in moderate to good yields. Highly chemoselective allylation is also described. The ketal and aryl acetal could be selectively allylated over the aliphatic one in 80-84% yields.