Enantioselective Ni–Al Bimetallic Catalyzed<i>exo</i>-Selective C–H Cyclization of Imidazoles with Alkenes

Wang, Yin–Xia; Qi, Shaolong; Luan, Yu‐Xin; Han, Xingwang; Wang, Shan; Chen, Hao; Ye, Mengchun

doi:10.1021/jacs.8b02547

Cited by 130 publications

(81 citation statements)

References 87 publications

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“…Recently, a method for enantioselective C−H cyclization of imidazole with alkene catalyzed by secondary phosphine oxide ligands was developed. The method was extended on benzimidazoles, and imidazopyridines …”

Section: Figurementioning

confidence: 99%

Annelated Aminoimidazoles in Synthesis of Imidazo[4,5‐b]pyridines

et al. 2019

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A convenient method for the synthesis of annelated imidazo[4,5‐b]pyridines was developed. The method is based on condensation of previously unavailable aminoimidazoles with 1,3‐dicarbonyl compounds. Aminoimidazoles 3 were prepared and some their properties were studied. The method gives the target imidazopyridines in good yields and allow varying substituents. A set of imidazopyridines was prepared. As an example, the imidazopyridines featuring carboxylic acids and esters were synthesized. Their structure was unambiguously determined by multinuclear NMR spectroscopy and the molecular structure of imidazopyridine 15 a was determined by single‐crystal X‐Ray diffraction.

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Section: Figurementioning

confidence: 99%

Annelated Aminoimidazoles in Synthesis of Imidazo[4,5‐b]pyridines

et al. 2019

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“…In this system, Al III would perform a dual role: that of a Lewis acid activator as in the reaction reported by Hiyama and co‐workers, and that of an anchoring site for the SPO ligand. Following this hypothesis, we investigated our previously reported Taddol‐derived SPO ( L 1 ) for the reaction . Without or with AlMe 3 , traditional phosphines and carbenes did not produce any of the desired product 3 a , except for some side products from decarbonylation and hydrocarbomoylation .…”

Section: Methodsmentioning

confidence: 99%

Enantioselective Twofold C−H Annulation of Formamides and Alkynes without Built‐in Chelating Groups

et al. 2020

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Twofold C−H annulation of readily available formamides and alkynes without built‐in chelating groups was achieved. Ni−Al bimetallic catalysis enabled by a bulky BINOL‐derived chiral secondary phosphine oxide (SPO) ligand proved to be critical for high reactivity and high selectivity. This reaction uses readily available formamides as starting materials and provides a concise synthetic pathway to a broad range of chiral ferrocenes in 40–98 % yield and 93–99 % ee.

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“…[31] In contrast, Ye et al reported on the nickel-catalyzed asymmetric exo-selective hydroarylation of alkenes with tethered imidazole derivatives (Scheme 7). [32] Here,t he TADDOL-based HASPO preligand 23 promoted nickel-aluminum bimetallic catalysis. Such TADDOL-SPOs had previously been employed in asymmetric organocatalysis, [33] but their use in enantioselective transitionmetal catalysis had remained limited.…”

Section: Càha Ctivation Of (Hetero)arenes 321 Intramolecular Reactmentioning

confidence: 97%

Enantioselective C−H Activation with Earth‐Abundant 3d Transition Metals

et al. 2019

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Molecular syntheses largely rely on time‐ and labour‐intensive prefunctionalization strategies. In contrast, C−H activation represents an increasingly powerful approach that avoids lengthy syntheses of prefunctionalized substrates, with great potential for drug discovery, the pharmaceutical industry, material sciences, and crop protection, among others. The enantioselective functionalization of omnipresent C−H bonds has emerged as a transformative tool for the step‐ and atom‐economical generation of chiral molecular complexity. However, this rapidly growing research area remains dominated by noble transition metals, prominently featuring toxic palladium, iridium and rhodium catalysts. Indeed, despite significant achievements, the use of inexpensive and sustainable 3d metals in asymmetric C−H activations is still clearly in its infancy. Herein, we discuss the remarkable recent progress in enantioselective transformations via organometallic C−H activation by 3d base metals up to April 2019.

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Enantioselective Ni–Al Bimetallic Catalyzedexo-Selective C–H Cyclization of Imidazoles with Alkenes

Cited by 130 publications

References 87 publications

Annelated Aminoimidazoles in Synthesis of Imidazo[4,5‐b]pyridines

Annelated Aminoimidazoles in Synthesis of Imidazo[4,5‐b]pyridines

Enantioselective Twofold C−H Annulation of Formamides and Alkynes without Built‐in Chelating Groups

Enantioselective C−H Activation with Earth‐Abundant 3d Transition Metals

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