66644-32-4Relevant academic research and scientific papers
Oxidant- and additive-free simple synthesis of 1,1,2-triiodostyrenes by one-pot decaroboxylative iodination of propiolic acids
Ghosh, Subhankar,Ghosh, Rajat,Chattopadhyay, Shital K.
supporting information, (2020/09/15)
A metal- and oxidant-free facile synthesis of a range of 1,1,2-triiodostryrene derivatives has been developed which utilizes a simple decarboxylative triiodination of propiolic acids using molecular iodine and sodium acetate in a one-pot manner. Electron-
Geometric E→Z Isomerisation of Alkenyl Silanes by Selective Energy Transfer Catalysis: Stereodivergent Synthesis of Triarylethylenes via a Formal anti-Metallometallation
Fa?bender, Svenja I.,Molloy, John J.,Mück-Lichtenfeld, Christian,Gilmour, Ryan
supporting information, p. 18619 - 18626 (2019/11/16)
An efficient geometrical E→Z isomerisation of alkenyl silanes is disclosed via selective energy transfer using an inexpensive organic sensitiser. Characterised by operational simplicity, short reaction times (2 h), and broad substrate tolerance, the reaction displays high selectivity for trisubstituted systems (Z/E up to 95:5). In contrast to thermal activation, directionality results from deconjugation of the π-system in the Z-isomer due to A1,3-strain thereby inhibiting re-activation. The structural importance of the β-substituent logically prompted an investigation of mixed bis-nucleophiles (Si, Sn, B). These versatile linchpins also undergo facile isomerisation, thereby enabling a formal anti-metallometallation. Mechanistic interrogation, supported by a theoretical investigation, is disclosed together with application of the products to the stereospecific synthesis of biologically relevant target structures.
A New Entry of Practical and Chemoselective Iodocarbenoids for Carbonyl Iodomethylenation
Yan, Tu-Hsin,Chen, Mei-Yuan
, p. 390 - 394 (2017/04/24)
Direct oxidative addition of CHI3 to the Mg-TiCl4 bimetallic species resulted in the generation of a highly chemoselective and practically convenient iodomethylenetitanium complex, which efficiently effected condensation even with enolizable or inert carbonyl compounds, such as sterically congested ketones, to provide vinyl iodide compounds.
Iron-Catalyzed e?Selective dehydrogenative borylation of vinylarenes with pinacolborane
Wang, Chao,Wu, Caizhi,Ge, Shaozhong
, p. 7585 - 7589 (2018/05/23)
We report the dehydrogenative borylation of vinylarenes with pinacolborane (HBpin) catalyzed by an iron(0) complex “(PMe3)4Fe”. A variety of monosubstituted and disubstituted vinylarenes underwent this iron-catalyzed transformation, affording E-vinyl boronate esters (VBEs) selectively in hi h ields. In addition we coupled this iron-catal zed dehydrogenative borylation with further transformations of the resulting vinyl boronate esters and developed various one-pot procedures for the functionalization of the vinylic C?H bonds in vinylarenes. Mechanistic studies reveal that this Fe-catalyzed reaction proceeds through syn-insertion of vinylarenes into a Fe-boryl species followed by β-hydrogen elimination from a syn coplanar conformation of the borylalkyl iron intermediate.
Copper-catalyzed direct alkenylation of N-iminopyridinium ylides
Mousseau, James J.,Bull, James A.,Charette, Andre B.
supporting information; experimental part, p. 1115 - 1118 (2010/05/17)
(Figure Presented) A versatile Cu-catalyzed direct C-H alkenylation of N-iminopyridinium ylides, compatible with several different copper sources (including a penny), provides a powerful and inexpensive method for the synthesis of functionalized pyridine derivatives. Chemoselective functionalization of halide-containing compounds allows the synthesis of alkenyl pyridines containing reactive tethers for further functionalization
Structure assignment of lagunapyrone B by fluorous mixture synthesis of four candidate stereoisomers
Yang, Fanglong,Newsome, Jeffery J.,Curran, Dennis P.
, p. 14200 - 14205 (2008/02/10)
Techniques of fluorous mixture synthesis have been used to make four candidate stereoisomers for the natural product lagunapyrone B. A quasiracemic mixture of vinyl iodides whose component configurations at C19-21 were encoded by fluorous silyl groups was
Halodephosphorylation of α,β-unsaturated phosphonic acid monoesters
Lahrache, Hind,Robin, Sylvie,Rousseau, Gérard
, p. 1635 - 1637 (2007/10/03)
Reaction of α,β-ethylenic and acetylenic phosphonic acid monoesters with (biscollidine)iodine(I) or (biscollidine)bromine(I) hexafluorophosphate led to α,β-unsaturated halides by, without precedent, dephosphorylation reactions.
A new Procedure for the Synthesis of (E)-1-iodo-1-alkenes
Martinez, A. Garcia,Alvarez, R. Martinez,Gonzalez, S. Martinez,Subramanian, L. R.,Conrad, M.
, p. 2043 - 2044 (2007/10/02)
(E)-1-iodo-1-alkenes 4 can be prepared stereoselectively from aldehydes 1 via IH-elimination of 1,1-di-iodoalkanes 3 with DBU. Key words: Vinyl iodide; diiodoalkane; elimination; stereoselectivity.
Nucleophilic and electrophilic properties of diiodomethyl lithium and sodium
Charreau, P.,Julia, M.,Verpeaux, J. N.
, p. 275 - 282 (2007/10/02)
The previously unreported diiodomethylsodium has been prepared; its thermal stability as well as nucleophilc behaviour (alkylation leading to 1,1-diiodoalkanes and allylation leading either to 1,1-diiodo-3-alkenes or 1-iodoalkadiene) are described and compared with the corresponding reactions of the lithium carbenoid.Alternatively, both lithium and sodium derivatives of diiodomethane react as electrophiles with α-sulfonyl carbanions to give 1-iodoalkenes in good yield.
