CuI-catalyzed cycloisomerization of propargyl amides

Alhalib, Ali; Moran, Wesley J.

doi:10.1039/c3ob42030b

Cited by 30 publications

(13 citation statements)

References 26 publications

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“…It is suggested that the N -(propargyl)thioamide intermediate A is initially formed, followed by a facile 5- exo-dig cyclization process to give the final products 46 in moderate yields (Scheme 12) [95]. …”

Section: Reviewmentioning

confidence: 99%

N-Propargylamines: versatile building blocks in the construction of thiazole cores

Arshadi

Vessally

Edjlali

et al. 2017

Beilstein J. Org. Chem.

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Thiazoles and their hydrogenated analogues are not only key structural units in a wide variety of natural products but they also constitute important building blocks in medicinal chemistry. Therefore, the synthesis of these compounds using new protocols is always interesting. It is well known that N-propargylamines can undergo a number of cyclization reactions to produce various nitrogen-containing heterocycles. In this review, we highlight the most important developments on the synthesis of thiazole and its derivatives starting from N-propargylamines. This review will be helpful in the development of improved methods for the synthesis of natural and biologically important compounds.

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Section: Reviewmentioning

confidence: 99%

N-Propargylamines: versatile building blocks in the construction of thiazole cores

Arshadi

Vessally

Edjlali

et al. 2017

Beilstein J. Org. Chem.

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“…Among all the candidate inorganic HTMs, CuI has received extensive atten-tion because of its wide band gap, high hole mobility [30][31][32][33], acceptable stability [34,35], and low cost [36][37][38]. Most importantly, CuI is non-hygroscopic [39][40][41][42]. In this study, we fabricate devices containing CuI as an HTM.…”

Section: Introductionmentioning

confidence: 99%

Phase degradation of all-inorganic perovskite CsPbI2Br films induced by a p-type CuI granular capping layer

Zhu

Feng

et al. 2020

Sci. China Mater.

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It is necessary to evaluate the interactions between the different functional layers in optoelectronic devices to optimize device performance. Recently, the I-rich allinorganic perovskite CsPbI 2 Br has attracted tremendous attention for use in solar cell applications because of its suitable band gap and favorable photo and thermal stabilities. It has been reported that the undesirable phase degradation of the photoactive α phase CsPbI 2 Br to the non-perovskite δ phase could be triggered by high humidity. To obtain stable devices, it is thus important to protect CsPbI 2 Br from moisture. In this paper, CuI, a non-hygroscopic p-type hole-transporting material, is found to induce the phase degradation of α-CsPbI 2 Br to the δ-CsPbI 2 Br. The rate and extent of phase degradation of CsPbI 2 Br are closely associated with the heating temperature and coverage of a CuI granular capping layer. This discovery is different from the widely reported water-induced phase degradation of CsPbI 2 Br. Our work highlights the importance of careful selection of hole-transporting materials during the processing of I-rich all-inorganic CsPbX 3 (X=Br, I) perovskites to realize high-performance optoelectronic devices.

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“…[3][4][5][6][7][8][9][10][11] Theinitial conversion, promoted by acid, was reported in 1962, [4] followed by the base catalyzed version via an allene intermediate in 1989. [5] In the recent two decades, significant progress has been made in this area with avariety of transition metal catalysts,i ncluding those of Au, [6] Ag, [7] Pd, [8] Cu, [9] Zn, [10] and others. [11] In these expanding studies, gold-catalyzed transformations have attracted the most attention in terms of the mechanism studies and synthetic applications (Scheme 1a).…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Allylation by Chiral Organocatalyst‐Promoted Formal Hetero‐Ene Reactions of Alkylgold Intermediates

et al. 2020

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An unprecedented catalytic asymmetric allylation of isatins and isatin-derived ketimines is reported enabled by agold and chiral organocatalyst cooperative catalysis strategy. This method offers expeditious access to chiral 2,5-disubsituted alkylideneoxazolines containing vicinal stereogenic centers, mainly in optically pure form, and which are otherwise impossible to access.Mechanistic evidence reveals the presence of an alkylgold intermediate,and an X-raycrystal structure of the allylgold species illuminates its unique stability and reactivity.A na symmetric formal hetero-ene reaction of this gold intermediate,i nvolving ad earomatization process,i s enabled with assistance of aq uinine-derived squaramide catalyst. This novel discovery extends the synthetic applications of gold complexes and the versatility of gold catalysis. Scheme 1. Gold-catalyzed transformations of N-propargylamides.

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CuI-catalyzed cycloisomerization of propargyl amides

Cited by 30 publications

References 26 publications

N-Propargylamines: versatile building blocks in the construction of thiazole cores

N-Propargylamines: versatile building blocks in the construction of thiazole cores

Phase degradation of all-inorganic perovskite CsPbI2Br films induced by a p-type CuI granular capping layer

Asymmetric Allylation by Chiral Organocatalyst‐Promoted Formal Hetero‐Ene Reactions of Alkylgold Intermediates

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