129215-15-2Relevant academic research and scientific papers
Bismuth mediated barbier synthesis of α-homoallylic alcohols via a sigmatropic rearrangement in [bmim][HSO4]
Chatterjee, Sucheta,Dey, Papiya,Kanojia, Seema V.,Chattopadhyay, Subrata,Goswami, Dibakar
supporting information, p. 765 - 775 (2020/12/13)
A novel protocol for the Bismuth metal mediated regioselctive crotylation of aldehydes yielding α-homoallylic alcohols has been developed using 20mol% [bmim][HSO4] as a metal activator, as well as a mediator for regioconversion from the initially formed γ-regiomer. The present protocol minimizes the use of conventional solvents and proceeds with good yields and excellent regioselectivities.
Distal Alkenyl C-H Functionalization via the Palladium/Norbornene Cooperative Catalysis
Dong, Guangbin,Fatuzzo, Nina,Wu, Zhao
supporting information, p. 2715 - 2720 (2020/03/10)
A distal-selective alkenyl C-H arylation method is reported through a directed palladium/norbornene (Pd/NBE) cooperative catalysis. The key is to use an appropriate combination of the directing group and the NBE cocatalyst. A range of acyclic and cyclic c
Direct, catalytic monofluorination of sp3 c-h bonds: A radical-based mechanism with ionic selectivity
Pitts, Cody Ross,Bloom, Steven,Woltornist, Ryan,Auvenshine, Dillon Jay,Ryzhkov, Lev R.,Siegler, Maxime A.,Lectka, Thomas
supporting information, p. 9780 - 9791 (2014/07/22)
Recently, our group unveiled a system in which an unusual interplay between copper(I) and Selectfluor effects mild, catalytic sp3 C-H fluorination. Herein, we report a detailed reaction mechanism based on exhaustive EPR, 19F NMR, UV-vis, electrochemical, kinetic, synthetic, and computational studies that, to our surprise, was revealed to be a radical chain mechanism in which copper acts as an initiator. Furthermore, we offer an explanation for the notable but curious preference for monofluorination by ascribing an ionic character to the transition state.
Ni-catalyzed stereoselective arylation of inert C-O bonds at low temperatures
Cornella, Josep,Martin, Ruben
supporting information, p. 6298 - 6301 (2014/01/17)
A Ni-catalyzed arylation of inert C-O bonds that operates at temperatures as low as -40 C is described. Unlike other methods for C-O bond cleavage utilizing organometallic species, this protocol operates at low temperatures, thus allowing the presence of sensitive functional groups with exquisite site-selectivity and stereoselectivity.
Allylation of carbonyl compounds mediated by Aluminum/Fluoride salts in water
Yuan, Shizhen,Liu, Jin,Xu, Ling,Zhu, Shaofeng
experimental part, p. 578 - 582 (2010/10/04)
A novel mediator (Al/KF) has been developed and employed in the Barbier-type alkylations of various aldehydes and ketones with alkyl halide in water. The carbonyl compounds could be effectively converted into corresponding homoallylic alcohol in good yiel
Asymmetric synthesis of α-substituted allyl boranes and their application in the synthesis of iso-agatharesinol
Fang, Guang Yu,Aggarwal, Varinder K.
, p. 359 - 362 (2007/10/03)
(Chemical Equation Presented) Use your borane: A stereocontrolled synthesis of allyl boranes from chiral sulfur ylides and their subsequent reaction with aldehydes to give homoallylic alcohols is described. The allyl boranes also could undergo a stereospe
A new cascade for the one-pot synthesis of linear homoallylic alcohols with an allylic diindium reagent
Hirashita,Yamamura,Kawai,Araki
, p. 387 - 388 (2007/10/03)
A new cascade based on a novel allylic diindium reagent has been developed; the indium reagent prepared from 3-bromo-1-iodopropene successively coupled with carbonyl compounds and then with aryl, alkenyl or allyl halides in the presence of a Pd(0) catalys
Tellurium in organic synthesis. Preparation of Z-vinylic cuprates from Z-vinylic tellurides and their reaction with enones and epoxides
Tucci, Fabio C.,Chieffi, Andre,Comasseto, Joao V.,Marino, Joseph P.
, p. 4975 - 4989 (2007/10/03)
Z-Vinylic tellurides, obtained with 100% stereoselectivity by the hydrotelluration of acetylenes, are easily transformed into Z-vinylic higher order cyanocuprates by reaction with preformed Me2-Cu(CN)Li2, W-Bu2Cu(CN)Lisub
On the Transmetallation of (E)-1-Phenyl-3-(tributylstannyl)propene and 3-Phenyl-3-(tributylstannyl)propene with BuSnCl3
Miyake, Hideyoshi,Yamamura, Kimiaki
, p. 1473 - 1474 (2007/10/02)
Transmetallation of (E)-1-phenyl-3-(tributylstannyl)propene and 3-phenyl-3-(tributylstannyl)propene with BuSnCl3, and the isomerization of the transmetallated product are described.The application of the reactions to stereoselective (Z)-3-phenyl-2-propenylation and threo-1-phenyl-2-propenylation of aldehydes is also described.
STEREOSELECTIVE HOMOALLYLIC ALCOHOL SYNTHESIS via SULPHONE α-CARBANION-MEDIATED COUPLING REACTIONS
Craig, Donald,Smith, Alison M.
, p. 2631 - 2632 (2007/10/02)
A novel method is described for the synthesis of homoallylic alcohols based on one-pot coupling reactions of sulphone stabilized carbanions with epoxides and aldehydes.
