49565-03-9Relevant articles and documents
Cyclic Alkenylsulfonyl Fluorides: Palladium-Catalyzed Synthesis and Functionalization of Compact Multifunctional Reagents
Lou, Terry Shing-Bong,Bagley, Scott W.,Willis, Michael C.
, p. 18859 - 18863 (2019/11/19)
A series of low-molecular-weight, compact, and multifunctional cyclic alkenylsulfonyl fluorides were efficiently prepared from the corresponding alkenyl triflates. Palladium-catalyzed sulfur dioxide insertion using the surrogate reagent DABSO effects sulfinate formation, before trapping with an F electrophile delivers the sulfonyl fluorides. A broad range of functional groups are tolerated, and a correspondingly large collection of derivatization reactions are possible on the products, including substitution at sulfur, conjugate addition, and N-functionalization. Together, these attributes suggest that this method could find new applications in chemical biology.
Palladium-catalyzed alkenylation and alkynylation of ortho-C(sp 2)-H bonds of benzylamine picolinamides
Zhao, Yingsheng,He, Gang,Nack, William A.,Chen, Gong
supporting information; experimental part, p. 2948 - 2951 (2012/08/07)
An efficient functionalization of ortho-C(sp2)-H bonds of picolinamide (PA)-protected benzylamine substrates with a range of vinyl iodides as well as acetylenic bromide is reported. ortho-Phenyl benzoic acid (oPBA) acts as an effective promoter in this reaction system. This method provides a practical strategy to access highly functionalized benzylamine compounds for organic synthesis.
Synthesis of highly substituted cyclobutane fused-ring systems from n-vinyl β-lactams through a one-pot domino process
Cheung, Lawrence L. W.,Yudin, Andrei K.
supporting information; experimental part, p. 4100 - 4109 (2010/07/05)
In this contribution, aminocyclobutanes, as well as eight-membered enamide rings, have been made from N-vinyl β-lactams. The eightmembered products have been formed by a [3,3]-sigmatropic rearrangement, whereas the aminocyclobutanes have been derived from a domino [3,3]-rearrangement/6π- electrocyclisation process. The aminocyclobutanes have been obtained in a highly diastereoselective fashion. The cyclobutane ring system tolerates fusion even if adjacent quaternary centres are present. Systems containing up to four fused rings are readily accessible. The reaction profile has been investigated by using Gaussian 03. This study suggests that two reaction pathways for aminocyclobutane formation are possible. In one pathway the [3,3]-sigmatropic rearrangement is the rate-limiting step and in the second pathway the electrocyclisation is rate limiting. Taken together, these reactions should facilitate the construction of fused heterocycles.
Ruthenium-catalyzed transformation of alkenyl triflates to alkenyl halides
Shirakawa, Eiji,Imazaki, Yusuke,Hayashi, Tamio
supporting information; experimental part, p. 5088 - 5090 (2009/12/08)
In the presence of a ruthenium catalyst, alkenyl triflates were found to be transformed to the corresponding bromides, chlorides and iodides simply by treatment with a lithium halide (1.2 equiv.). The Royal Society of Chemistry 2009.
Synthesis of aminocyclobutanes through ring expansion of N-vinyl-β-lactams
Cheung, Lawrence L. W.,Yudin, Andrei K.
supporting information; body text, p. 1281 - 1284 (2009/08/12)
Both eight-membered enamide rings and fused [4.2.0]aminocyclobutane- containing δ-lactams can be accessed from N-vinyl-β-lactams. The eight-membered rings are made through a [3,3] sigmatropic rearrangement. At elevated temperature, the eight-membered lact
Procedures for the nickel-catalyzed conversion of olefinic and cycloolefinic chlorides into iodides
Hooijdonk,Peters,Vasilevsky,Brandsma
, p. 1261 - 1263 (2007/10/02)
A number of olefinic and cycloolefinic chlorides have been converted into the corresponding iodides by treatment with an excess of sodium iodide in dimethylformamide in the presence of bis(1,5-cyclooctadienyl)nickel or a mixture of nickel bromide and zinc
The Reaction of Vinyl Phosphates with Iodotrimethylsilane: Synthesis of Vinyl Iodides from Ketones
Lee, Koo,Wiemer, David F.
, p. 2433 - 2436 (2007/10/02)
A new method for preparation of vinyl iodides from ketones is described, based on the reaction of vinyl phosphates with iodotrimethylsilane.
A New Method for Cyclopentanone Annelation
Snider, Barry B.,Cartaya-Marin, Claudia P.
, p. 153 - 157 (2007/10/02)
MeAlCl2-initiated cyclization of enone 6d provides an 85percent yield of a 9:1 mixture of trans- and cis-fused hydroazulenones 9 and 10.Similarly, cyclization of 7d gives a 31percent yield of 11 with an equatorial methyl group, and cyclization of 8d affor
Photochemistry of Alkyl Halides. 10. Vinyl Halides and Vinylidene Dihalides
Kropp, Paul J.,McNeely, Steven A.,Davis, Robert Drummond
, p. 6907 - 6915 (2007/10/02)
The photobehavior of the acyclic vinyl iodide 2, the 1-iodocycloalkenes 11-14 and 39, the (halomethylene)cycloalkanes 45-48, and the (dihalomethylene)cyclohexanes 62-64 has been studied.Except for the dichloride 64, which exhibited only radical behavior, each of the halides afforded a mixture of ionic and radical products.The two bromides studied, 48 and 63, afforded lower ratios of ionic to radical products than the corresponding iodides 45 and 62.Irradiation of vinyl iodides was found to be a convenient and powerful method for the generation of vinyl cations, including the highly strained 1-cyclohexenyl and 1-cyclopentenyl cations and the unstabilized α-unsubstituted cations 51 and 54.The latter cations underwent rearrangement to the ring-expanded 1-cycloalkenyl cations 28 and 36, respectively.Lowering the temperature of the irradiation of iodides 13, 14, and 45 resulted in an increased ratio of ionic to radical products.However, iodide 47, which underwent principally fragmentation to enyne 61, showed little temperature effect.
