3027-03-0Relevant articles and documents
Pd-Catalyzed Double-Decarbonylative Aryl Sulfide Synthesis through Aryl Exchange between Amides and Thioesters
Bie, Fusheng,Cao, Han,Liu, Chengwei,Liu, Xuejing,Shi, Yijun,Szostak, Michal,Zhou, Tongliang
supporting information, p. 8098 - 8103 (2021/10/25)
We report the palladium-catalyzed double-decarbonylative synthesis of aryl thioethers by an aryl exchange reaction between amides and thioesters. In this method, amides serve as aryl donors and thioesters are sulfide donors, enabling the synthesis of valuable aryl sulfides. The use of Pd/Xantphos without any additives has been identified as the catalytic system promoting the aryl exchange by C(O)-N/C(O)-S cleavages. The method is amenable to a wide variety of amides and sulfides.
Cross-dehydrogenative coupling of acetanilides with aromatic aldehydes
Kianmehr, Ebrahim,Afaridoun, Hadi
supporting information, p. 4319 - 4323 (2020/03/26)
Potassium bromide mediated cross-dehydrogenative coupling of acetanilides with aromatic aldehydes in the presence of tert-butyl hydroperoxide (TBHP) for the synthesis of imides has been developed. This new and efficient approach was carried out under an air atmosphere at room temperature and the desired products were obtained in good to high yields.
Hypervalent Iodine-Mediated Oxidative Rearrangement of N-H Ketimines: An Umpolung Approach to Amides
Zhao, Zhenguang,Peng, Zhiyuan,Zhao, Yongli,Liu, Hao,Li, Chongnan,Zhao, Junfeng
, p. 11848 - 11853 (2017/11/28)
An umpolung approach to amides via hypervalent iodine-mediated oxidative rearrangement of N-H ketimines under mild reaction conditions is described. This strategy provides target amides with excellent selectivity in good yields. In addition, preliminary m
Imide synthetic method of compound
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Paragraph 0048-0050, (2017/04/20)
The invention relates to a synthesis method of an imide compound. The method takes an FeCl2/assistant catalytic system to promote efficient synthesis of the imide compound, and optimizes the optimal combination of components by a single factor experiment approach so as to obtain the best compound catalytic system. The preparation technology opens up the preparation method of the imide compound and has high reaction yield, thus having broad large-scale application prospects and potential market value.
Fe-Catalysed oxidative C-H/N-H coupling between aldehydes and simple amides
Wang, Jing,Liu, Chao,Yuan, Jiwen,Lei, Aiwen
supporting information, p. 4736 - 4739 (2014/05/06)
A novel oxidative coupling of aldehydes with simple amides, most likely involving a radical process, was achieved through the use of an iron catalyst. Various amides were utilized as substrates to easily construct imides by coupling with aldehydes. A catalytic cycle involving the benzoyl halide intermediate is proposed based on our experimental results. This journal is the Partner Organisations 2014.
Reaction of electron-deficient N=N, N=O double bonds, singlet oxygen, and CC triple bonds with acyloxyketenes or mesoionic 1,3-dioxolium-4-olates: Generation of unstable mesoionic 1,3-dioxolium-4-olates from acyloxyketenes
Hamaguchi, Masashi,Tomida, Naoki,Iyama, Yuji
, p. 1326 - 1334 (2007/10/03)
(Chemical Equation Presented) Reactions of azodicarboxylates and nitrosobenzene derivatives with acyloxyketenes generated from dehydrochlorination of α-acyloxyarylacetyl chlorides were carried out to give triacylbenzamidine and N-arylimide derivatives, respectively, in good yields. The same compounds were obtained from the reaction with mesoionic 1,3-dioxolium-4-olates generated by Rh2(OAc)4-catalyzed decomposition of aryldiazoacetic anhydride derivatives. Formation of the same compounds from the different starting materials indicates that their reactions involve the same intermediates. The formation of triacylbenzamidine and N-arylimide derivatives is explained by 1,3-dipolar cycloaddition between electron-deficient N=N or N=O bonds and mesoionic 1,3-dioxolium-4-olates following by decarboxylation, ring opening of the resultant carbonyl ylides, and subsequent Mumm rearrangement of the corresponding imidates. The reaction with singlet oxygen composed of more electronegative atoms than N=N and N=O bonds also gave products arising from the singlet oxygen adducts with 1,3-dioxolium-4-olates. The generation of less stable mesoionic 1,3-dioxolium-4-olates from acyloxyketenes was also confirmed by isolation of furandicarboxylates on generation of acyloxyketenes from α- acyloxyarylacetyl chlorides in the presence of reactive dipolarophile dimethyl acetylenedicarboxylate.
Reactions of thioamides with metal carboxylates in organic media
Avalos, Martin,Babiano, Reyes,Cintas, Pedro,Duran, Carlos J.,Higes, Francisco J.,Jimenez, Jose L.,Lopez, Ignacio,Palacios, Juan C.
, p. 14463 - 14480 (2007/10/03)
Reactions of thioamides with metal carboxylates in organic solvents are described. These processes enable the selective preparation of nitriles, imides or amides depending on the substitution pattern of the starting material. Mechanistic hypotheses supported by experimental evidences, including the unequivocal synthesis of bis(thioacetanilide)mercury(II) as a key reaction intermediate, are also proposed.
Reaction of Thioamides with Silver Carboxylates in Aprotic Media. A Nucleophilic Approach to the Synthesis of Imides, Amides, and Nitriles.
Avalos, Martin,Babiano, Reyes,Duran, Carlos J.,Jimenez, Jose L.,Palacios, Juan C.
, p. 477 - 480 (2007/10/02)
Synthesis of nitriles, imides, and amides by reaction of silver carboxylates with unsubstituted, N-substituted, and N,N-disubstituted thiomaides in aprotic media are described.
Reaction of Arenediazonium Salts with Nitriles in the Presence of Sodium Carboxylates. A Convenient Synthesis of Unsymmetrical N-Aryl Acyclic Imides
Kikukawa, Kiyoshi,Kono, Kiyoshi,Wada, Fumio,Matsuda, Tsutomu
, p. 3671 - 3672 (2007/10/02)
Reactions of arenediazonium tetrafluoroborates (ArN2BF4), acetonitrile and sodium carboxylates (RCOONa) gave N-acyl acetanilides (ArN(COR)COCH3) in moderate to good yields (Ar=Ph, 2-MeC6H4, 3-MeC6H4, 4-MeC6H4, 2,6-(Me)2C6H3; R=Et, i-Pr, t-Bu, Ph).Acrylonitrile and benzonitrile could be used in the reaction instead of acetonitrile.
The Isoimide-Imide Rearrangement
Brady, Kieran,Hegarty, Anthony F.
, p. 121 - 126 (2007/10/02)
When imidoyl chlorides (8) are solvolysed in the pH range 3-13 in aqueous dioxan in the presence of acetate or benzoate ions, the isoimides (10) are formed in situ.These isoimides undergo acid (pH 11.5) catalysed acyl transfer to the solvent, giving the amides (12).But at intermediate pH (6-11) rearrangement to the N-acyl form (11) ( the Mumm rearrangement) alone occurs.The specific rate of this O N acyl group migration is pH independent and shows a low solvent effect (m 0.175).Substituents attached to carbon or nitrogen have the same effect (ρ -0.84).When the migrating group R is varied a non-linear Hammet plot is observed, with ρ +0.60 for electron-withdrawing and +1.65 for electron-donating substituents.The changeover point is a function of the migrating terminus varying from R=Ph (when Y=H) to R=p-tolyl (when Y=p-NO2).Rate-determining O N acyl transfer is suggested in all cases, but this is preceded by an equilibrium which favours the Z form (10a) when R is electron donating.
