- Palladium-Catalyzed Desulfurative Hiyama Coupling of Thioureas to Achieve Amides via Selective C-N Bond Cleavage
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Palladium-catalyzed Hiyama coupling of active thioureas via selective C-N bond cleavage is reported. Notably, the new approach employed active thioureas as coupling partners in the presence of arylsilanes to give amides in good yield. Further, this strategy, which utilized CuF 2as a key oxidant and activator, afforded various amide products under mild conditions and an easy to handle procedure without extra base.
- He, Zhanyu,Yan, Chu,Zhang, Mei,Irfan, Majeed,Wang, Zijia,Zeng, Zhuo
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p. 705 - 710
(2021/10/25)
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- Nickel-Catalyzed Oxidative Transamidation of Tertiary Aromatic Amines with N -Acylsaccharins
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The use of tertiary amines as surrogates for secondary amines has prominent advantages in terms of stabilization and ease of handling. A Ni-catalyzed transamidation of N -acylsaccharins with tertiary aromatic amines is reported. By using tert -butyl hydroperoxide as the terminal oxidant, this reaction permits selective cleavage of the C(sp 3)-N bonds of unsymmetrical tertiary aromatic amines depending on the sizes of the alkyl substituents.
- Liu, Shengzhang,Yang, Lingyun,Tao, Jiasi,Yu, Weijie,Wang, Tao,Fu, Junkai
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supporting information
p. 1642 - 1646
(2021/06/21)
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- Palladium-Catalyzed Desulfurative Amide Formation from Thioureas and Arylboronic Acids
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The development of the reactivity on carbene complexes would lead to the creation of novel synthetic strategies. We discovered herein the Pd-catalyzed desulfurative amide formation involved Suzuki-Miyaura coupling reaction, notably the Pd complex was generated in situ from thioureas, Ag salt and Pd catalyst. Silver salt was essential for the construction of this type of carbenes from available and stable thioureas and well participated in the catalytic cycle. We report a method for the synthesis of arylamides from arylboronic acids, which greatly enriched the application of thiourea chemistry and expanded the application of the Suzuki-Miyaura coupling.
- Su, Jianke,Li, Wendong,Li, Xin,Xu, Jian,Song, Qiuling
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p. 5664 - 5668
(2020/10/02)
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- Catalytic Hydrogenation of Carboxamides with a Bifunctional Cp Ru Catalyst Bearing an Imidazol-2-ylidene with a Protic Aminoethyl Side Chain
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Synthesis of a Cp Ru complex bearing an NH 2 -functionalized N -heterocyclic carbene (C-N H) was achieved by treatment of CpRuBr(isoprene) with an equimolar amount of a silver complex, which was generated from Ag 2 O and 1-(2-aminoethyl)-3-methylimidazolium bromide, in CH 3 CN at room temperature. The new CpRuBr(C-N H) complex showed a higher catalytic performance than the related CpRuCl(P-N H) and CpRuCl(N-N H) complexes. In the reaction of N -arylcarboxamides, the amine products were obtained in satisfactory yields under mild temperature conditions.
- Ikariya, Takao,Kawano, Teruhiro,Kayaki, Yoshihito,Watari, Ryo
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p. 2542 - 2547
(2019/06/08)
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- Formamide as an Unconventional Amine Protecting Group for PET Radiochemistry
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We developed a versatile, rapid, and robust high-yielding radiochemistry-adapted protocol utilizing formamides as masking groups for secondary and tertiary amines. Selective reducing conditions were devised using borane reagents. In this protocol formamid
- Jakobsson, Jimmy Erik,Gr?nnevik, Gaute,Rafique, Waqas,Hartvig, Karoline,Riss, Patrick Johannes
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supporting information
p. 3701 - 3704
(2018/07/31)
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- Intensified Microwave-Assisted N-Acylation Procedure - Synthesis and Activity Evaluation of TRPC3 Channel Agonists with a 1,3-Dihydro-2H-benzo[d]imidazol-2-one Core
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Upon controlled microwave heating and using cyanuric chloride as a coupling reagent, an efficient amidation procedure for the synthesis of 1,3-dihydro-2H-benzo[d]imidazol-2-one-based agonists of TRPC3/6 ion channels has been developed. Compared to the few conventional protocols, a drastic reduction in processing time from ca. 2 days down to 10 minutes was achieved accompanied by significantly improved product yields. The robustness of the method was confirmed by 18 additional examples including aromatic, aliphatic, and heterocyclic amines and acids. The obtained agonists were screened for biological activity at 1 μM concentration and few structure-activity relations have been established.
- Guedes de La Cruz, Gema,Svobodova, Barbora,Lichtenegger, Michaela,Tiapko, Oleksandra,Groschner, Klaus,Glasnov, Toma
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p. 695 - 700
(2017/03/21)
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- Palladium-catalyzed aminocarbonylation of aryl iodides with amides and N-alkyl anilines
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A novel and efficient palladium-catalyzed aminocarbonylation of aryl iodides with amides and N-alkyl anilines has been developed. The reaction tolerates a wide range of functional groups and is a reliable method for the rapid synthesis of a variety of valuable imides and tertiary benzanilides under an atmospheric pressure of CO. Copyright
- Ran, Longfei,Ren, Zhi-Hui,Wang, Yao-Yu,Guan, Zheng-Hui
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p. 577 - 583
(2014/02/14)
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- NBu4NI-catalyzed oxidative amidation of aldehydes with tertiary amines
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An efficient oxidative coupling protocol for amide formation has been developed. Various tertiary amines and aromatic aldehydes were oxidized to their corresponding tertiary amides in moderate to good yields in the presence of a simple nBu4NI-catalyst.
- Wang, Shan,Wang, Jian,Guo, Rui,Wang, Gao,Chen, Shan-Yong,Yu, Xiao-Qi
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supporting information
p. 6233 - 6236
(2013/10/22)
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