Palladium-Catalyzed C–H Functionalization of Aromatic Oximes: A Strategy for the Synthesis of Isoquinolines

Zhu, Zhongzhi; Tang, Xiaodong; Li, Xianwei; Wu, Wanqing; Deng, Guohua; Jiang, Huanfeng

doi:10.1021/acs.joc.5b02376

Cited by 69 publications

(46 citation statements)

References 54 publications

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“…[11][12][13] The latter is also well catalyzed by metal oxides or Me 3 SiCl. [15][16][17] Amongt he various Lewis acids, the activity of which towards aldehydes was examined, beryllium species, which are among the hardest known Lewis acids, have never been investigated. Only one beryllium aldehydec ompound-ab enzaldehydea dduct towards BeCl 2 of whichn or eactivity had been investigated-was known so far.…”

Section: Introductionmentioning

confidence: 99%

Beryllium‐Induced Conversion of Aldehydes

Müller

Buchner

2019

Chemistry A European J

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Aldehydes play a key role in the human metabolism. Therefore, it is essential to know their reactivity with beryllium compounds in order to assess its effects in the body. The reactivity of simple aldehydes towards beryllium halides (F, Cl, Br, I) was studied through solution and solid‐state techniques and revealed distinctively different reactivities of the beryllium halides, with BeF2 being the least and BeI2 the most reactive. Rearrangement and aldol condensation reactions were observed and monitored by in situ NMR spectroscopy. Crystal structures of various compounds obtained by Be2+‐catalyzed cyclization, rearrangement, and aldol addition reactions or ligation of beryllium halides have been determined, including unprecedented one‐dimensional BeCl2 chains and the first structurally characterized example of an 1‐iodo‐alkoxide. Long‐term studies showed that only aldehydes without a β‐H can form stable beryllium complexes, whereas other aldehydes are oligo‐ and polymerized or decomposed by beryllium halides.

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Section: Introductionmentioning

confidence: 99%

Beryllium‐Induced Conversion of Aldehydes

Müller

Buchner

2019

Chemistry A European J

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“…The best optimized condition was applied to various aryl oximes 92 and (1-azidovinyl)benzene 262 to obtain the desired product in moderate to excellent yields (Scheme 154). [155] In addition, they also envisioned the formation of isoquinoline by homocoupling of aryloxime with the increase of temperature and prolonging the reaction time to 24 hours (Scheme 155).…”

Section: Pd-catalyzed Isoquinoline Synthesismentioning

confidence: 99%

Comprehensive Strategies for the Synthesis of Isoquinolines: Progress Since 2008

2020

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In the past decades, an enormous number of reports have been dedicated towards the synthesis of nitrogen containing heterocycles. This immense interest have emerged owing to their wide varieties of pharmacological activities. The present review focused on the synthesis of isoquinoline derivatives, a family of N-heterocycles showing a broad range of structural diversity, biological and pharmaceutical activities. The progress on their synthetic strategies using versatile approaches are discussed in details.

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“…Substituted isoquinolines 51 have been prepared through the Pd(II)-catalyzed coupling of vinyl azides with oximes 47 (Scheme 15). 53 In this process, the oxime is proposed to act as an internal directing group for ortho C-H activation by the Pd(II) catalyst. The resulting palladacycle (not shown) can undergo migratory insertion with the 2H-azirine to give intermediate 48, 54 which on reductive elimination gives oxime acetate 49. developed which delivers unusual 1-azabicyclo[3.1.0]hexane scaffolds 60 with excellent diastereoselectivity (Scheme 17).…”

Section: Amentioning

confidence: 99%

α-Substituted vinyl azides: an emerging functionalized alkene

et al. 2017

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Vinyl azides are highly versatile synthons that provide access to numerous N-heterocycles and other functional groups. α-Substituted vinyl azides (azido vinylidenes) are a special class that display unique reactivity, able to react not only as azides, but also as radical acceptors, enamine-type nucleophiles, and even electrophiles, thus delivering a wide range of nitrogen-containing compounds and their derivatives. An impressive variety of intermediates - such as iminodiazonium ions, nitrilium ions, iminyl radicals, and metal enaminyl radicals - can be generated from vinyl azides and exploited in cycloadditions, C-H functionalizations, hydrolysis processes, and cascade reactions under transition metal/photoredox catalysis. In addition to presenting synthetic protocols to access vinyl azides, this Review offers a comprehensive coverage of the development of their multifaceted reactivity, and highlights their potential as versatile precursors for synthetic applications.

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Palladium-Catalyzed C–H Functionalization of Aromatic Oximes: A Strategy for the Synthesis of Isoquinolines

Cited by 69 publications

References 54 publications

Beryllium‐Induced Conversion of Aldehydes

Beryllium‐Induced Conversion of Aldehydes

Comprehensive Strategies for the Synthesis of Isoquinolines: Progress Since 2008

α-Substituted vinyl azides: an emerging functionalized alkene

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