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Thematische Bibliographien / Formation of C-N bonds

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Zeitschriftenartikel

Auswahl der wissenschaftlichen Literatur zum Thema „Formation of C-N bonds“

Autor: Grafiati

Veröffentlicht am 25. Mai 2024

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Zeitschriftenartikel zum Thema "Formation of C-N bonds"

1

Meng, Ge, Pengfei Li, Kai Chen, and Linghua Wang. "Recent Advances in Transition-Metal-Free Aryl C–B Bond Formation." Synthesis 49, no. 21 (2017): 4719–30. http://dx.doi.org/10.1055/s-0036-1590913.

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Arylboronic acids and their derivatives are widely used in organic synthesis. Conventional methods for their preparation require either reactive organometallic reagents or transition-metal-mediated processes. In recent years, transition-metal-free reactions for aryl C–B bond formation that obviate preformed organometallic reagents have gained interest and have developed rapidly. These new reactions have shown significant advantages for the preparation of functionalized molecules. In this review, an overview of the recent advances in transition-metal-free aromatic borylation reactions is provided.1 Introduction2 Transition-Metal-Free Transformations of CAr–N Bonds to CAr–B Bonds3 Transition-Metal-Free Transformations of CAr–X Bonds to CAr–B Bonds4 Transition-Metal-Free Transformations of CAr–H Bonds to CAr–B Bonds5 Conclusion

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2

Zeng, Xiaoming, and Xuefeng Cong. "Chromium-Catalyzed Cross-Coupling Reactions by Selective Activation of Chemically Inert Aromatic C–O, C–N, and C–H Bonds." Synlett 32, no. 13 (2021): 1343–53. http://dx.doi.org/10.1055/a-1507-4153.

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AbstractTransition-metal-catalyzed cross-coupling has emerged as one of the most powerful and useful tools for the formation of C–C and C–heteroatom bonds. Given the shortage of resources of precious metals on Earth, the use of Earth-abundant metals as catalysts in developing cost-effective strategies for cross-coupling is a current trend in synthetic chemistry. Compared with the achievements made using first-row nickel, iron, cobalt, and even manganese catalysts, the group 6 metal chromium has rarely been used to promote cross-coupling. This perspective covers recent advances in chromium-catalyzed cross-coupling reactions in transformations of chemically inert C(aryl)–O, C(aryl)–N, and C(aryl)–H bonds, offering selective strategies for molecule construction. The ability of low-valent Cr with a high-spin state to participate in two-electron oxidative addition is highlighted; this is different from the mechanism involving single-electron transfer that is usually assigned to chromium-mediated transformations.1 Introduction2 Chromium-Catalyzed Kumada Coupling of Nonactivated C(aryl)–O and C(aryl)–N Bonds3 Chromium-Catalyzed Reductive Cross-Coupling of Two Nonactivated C(aryl)–Heteroatom Bonds4 Chromium-Catalyzed Functionalization of Nonactivated C(aryl)–H Bonds5 Conclusions and Outlook

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3

Henry, Martyn, Mohamed Mostafa, and Andrew Sutherland. "Recent Advances in Transition-Metal-Catalyzed, Directed Aryl C–H/N–H Cross-Coupling Reactions." Synthesis 49, no. 20 (2017): 4586–98. http://dx.doi.org/10.1055/s-0036-1588536.

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Amination and amidation of aryl compounds using a transition-metal-catalyzed cross-coupling reaction typically involves prefunctionalization or preoxidation of either partner. In recent years, a new class of transition-metal-catalyzed cross-dehydrogenative coupling reaction has been developed for the direct formation of aryl C–N bonds. This short review highlights the substantial progress made for ortho-C–N bond formation via transition-metal-catalyzed chelation-directed aryl C–H activation and gives an overview of the challenges that remain for directed meta- and para-selective reactions.1 Introduction2 Intramolecular C–N Cross-Dehydrogenative Coupling2.1 Nitrogen Functionality as Both Coupling Partner and Directing Group2.2 Chelating-Group-Directed Intramolecular C–N Bond Formation3 Intermolecular C–N Cross-Dehydrogenative Coupling3.1 ortho-C–N Bond Formation3.1.1 Copper-Catalyzed Reactions3.1.2 Other Transition-Metal-Catalyzed Reactions3.2 meta- and para-C–N Bond Formation4 C–N Cross-Dehydrogenative Coupling of Acidic C–H Bonds5 Conclusions

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4

Chang, Denghu, Dan Zhu, Peng Zou, and Lei Shi. "Cleavage of C–N bonds in guanidine derivatives and its relevance to efficient C–N bonds formation." Tetrahedron 71, no. 11 (2015): 1684–93. http://dx.doi.org/10.1016/j.tet.2015.01.050.

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5

Wang, Congyang, and Ting Liu. "Manganese-Catalyzed C(sp2)–H Addition to Polar Unsaturated Bonds." Synlett 32, no. 13 (2021): 1323–29. http://dx.doi.org/10.1055/a-1468-6136.

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AbstractTransition-metal-catalyzed nucleophilic C–H addition of hydrocarbons to polar unsaturated bonds could intrinsically avoid prefunctionalization of substrates and formation of waste byproducts, thus featuring high step- and atom-economy. As the third most abundant transition metal, manganese-catalyzed C–H addition to polar unsaturated bonds remains challenging, partially due to the difficulty in building a closed catalytic cycle of manganese. In the past few years, we have developed manganese catalysis to enable the sp2-hydrid C–H addition to polar unsaturated bonds (e.g., imines, aldehydes, nitriles), which will be discussed in this personal account.1 Introduction2 Mn-Catalyzed N-Directed C(sp2)–H Addition to Polar Unsaturated Bonds3 Mn-Catalyzed O-Directed C(sp2)–H Addition to Polar Unsaturated Bonds4 Conclusion

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6

Rit, Raja K., Majji Shankar, and Akhila K. Sahoo. "C–H imidation: a distinct perspective of C–N bond formation." Organic & Biomolecular Chemistry 15, no. 6 (2017): 1282–93. http://dx.doi.org/10.1039/c6ob02162j.

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7

Zinser, Caroline M., Katie G. Warren, Fady Nahra, et al. "Palladate Precatalysts for the Formation of C–N and C–C Bonds." Organometallics 38, no. 14 (2019): 2812–17. http://dx.doi.org/10.1021/acs.organomet.9b00326.

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8

Wei, Wenting, Wenming Zhu, Yi Wu, Yiling Huang, and Hongze Liang. "Progress in C—N Bonds Formation Using t-BuONO." Chinese Journal of Organic Chemistry 37, no. 8 (2017): 1916. http://dx.doi.org/10.6023/cjoc201703039.

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9

Zhao, Binlin, Torben Rogge, Lutz Ackermann, and Zhuangzhi Shi. "Metal-catalysed C–Het (F, O, S, N) and C–C bond arylation." Chemical Society Reviews 50, no. 16 (2021): 8903–53. http://dx.doi.org/10.1039/c9cs00571d.

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10

Sun, Qiu, Ling He, Jiaxin Cheng, Ze Yang, Yuansheng Li, and Yulan Xi. "Synthesis of Isoxazolines and Isoxazoles via Metal-Free Desulfitative Cyclization." Synthesis 50, no. 12 (2018): 2385–93. http://dx.doi.org/10.1055/s-0037-1609480.

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A novel, one-pot reaction for the synthesis of isoxazolines and isoxazoles is developed via a cascade process under metal-free conditions. The approach involves the formation of intramolecular C–N and C–O bonds and intermolecular C–C bonds from aromatic alkenes or alkynes and N-hydroxysulfonamides using hypervalent iodine(VII) and iodine as the oxidant. Activation of C–H and C–C bonds/construction of C–O bonds/elimination of SO2/C–N bond formation is achieved in sequence in the reaction system.

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