Cobalt‐Catalyzed Oxidative Isocyanide Insertion to Amine‐Based Bisnucleophiles: Diverse Synthesis of Substituted 2‐Aminobenzimidazoles, 2‐Aminobenzothiazoles, and 2‐Aminobenzoxazoles

Zhu, Tong‐Hao; Wang, Shun‐Yi; Wang, Gao‐Nan; Ji, Shun‐Jun

doi:10.1002/chem.201300239

Cited by 77 publications

(29 citation statements)

References 76 publications

(18 reference statements)

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“…In 2013, Ji et al. reported the synthesis of 2‐aminobenzimidazoles, ‐benzoxazoles, and ‐benzothiazoles ( 137 ) via a Co II ‐catalyzed reaction of isocyanides with 2‐aminoanilines, 2‐aminophenols, and 2‐aminothiophenols ( 136 ), respectively (Scheme ) . This exemplifies that bisnucleophiles do not need to be diamines.…”

Section: Insertions Of Isocyanides Into Heteroatom–metal Bondsmentioning

confidence: 99%

Base Metal Catalyzed Isocyanide Insertions

et al. 2019

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Isocyanides are diverse C1 building blocks considering their potential to react with nucleophiles, electrophiles, and radicals. Therefore, perhaps not surprisingly, isocyanides are highly valuable as inputs for multicomponent reactions (MCRs) and other one‐pot cascade processes. In the field of organometallic chemistry, isocyanides typically serve as ligands for transition metals. The coordination of isocyanides to metal centers alters the electronic distribution of the isocyano moiety, and reaction pathways can therefore be accessed that are not possible in the absence of the metal. The tunable reactivity of the isocyanide functional group by transition metals has evolved into numerous useful applications. Especially palladium‐catalyzed isocyanide insertion processes have emerged as powerful reactions in the past decade. However, reports on the use of earth‐abundant and cheap base metals in these types of transformations are scarce and have received far less attention. In this Minireview, we focus on these emerging base metal catalyzed reactions and highlight their potential in synthetic organic chemistry. Although mechanistic studies are still scarce, we discuss distinct proposed catalytic cycles and categorize the literature according to 1) the (hetero)atom bound to and 2) the type of bonding with the transition metal in which the (formal) insertion occurs.

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Section: Insertions Of Isocyanides Into Heteroatom–metal Bondsmentioning

confidence: 99%

Base Metal Catalyzed Isocyanide Insertions

et al. 2019

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“…The organic segment is connected to the isocyanide group via the nitrogen atom, not via the carbon. They are used as privileged synthons for the synthesis of other organic compounds in particular various heterocycles [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] , frequently via multicomponent reactions (MCRs) namely isocyanide multicomponent reactions (IMCRs) 25,[38][39][40][41][42][43][44][45][46][47][48][49] . Noticeably isocyanides are susceptible to polymerization 50 .…”

Section: Introductionmentioning

confidence: 99%

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

2016

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“…[19] However, that method needed longer times at high temperature. It would be more efficient if the cobalt-catalyzed oxidative isocyanide insertion to amine-based bis-nucleophiles could be achieved under ultrasonic conditions.…”

Section: Resultsmentioning

confidence: 98%

Cobalt(II)‐Catalyzed Isocyanide Insertion Reaction with Amines under Ultrasonic Conditions: A Divergent Synthesis of Ureas, Thioureas and Azaheterocycles

Zhu

Cao

et al. 2014

Adv Synth Catal

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Abstract:Cobalt(II) acetylacetonate-catalyzed isocyaA C H T U N G T R E N N U N G nide insertion reactions with amines utilizing tert-butyl hydroperoxide (TBHP) as an oxidant under ultrasound conditions have been developed, which lead to the synthesis of ureas, thioureas, as well as 2-aminobenzimidazoles, 2-aminobenzothiazoles, and 2-aminobenzoxazoles under the general reaction conditions in up to 96% yields, respectively. The intermediate amino methylidyneaminiums, initiated by cobalt(II) acetylacetonate-catalyzed reactions of isocyanides with amines, could be easily trapped by different nucleophiles such as water, sulfur, and intramolecular nucleophilic functional groups. This method provides a simple, general and practical protocol for the divergent synthesis of ureas, thioureas and azaheterocycles.

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Cobalt‐Catalyzed Oxidative Isocyanide Insertion to Amine‐Based Bisnucleophiles: Diverse Synthesis of Substituted 2‐Aminobenzimidazoles, 2‐Aminobenzothiazoles, and 2‐Aminobenzoxazoles

Cited by 77 publications

References 76 publications

Base Metal Catalyzed Isocyanide Insertions

Base Metal Catalyzed Isocyanide Insertions

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

Cobalt(II)‐Catalyzed Isocyanide Insertion Reaction with Amines under Ultrasonic Conditions: A Divergent Synthesis of Ureas, Thioureas and Azaheterocycles

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