2010
DOI: 10.3390/molecules15118006
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Recent Advance in Heterocyclic Organozinc and Organomanganese Compounds; Direct Synthetic Routes and Application in Organic Synthesis

Abstract: A practical synthetic route for the preparation of 2-pyridyl and 3-pyridyl derivatives has been accomplished by utilizing a simple coupling reaction of stable 2-pyridylzinc bromides and 3-pyridylzinc bromides. The organozincs used in this study were easily prepared via the direct insertion of active zinc into the corresponding bromopyridines. The subsequent coupling reactions with a variety of different electrophiles have afforded the corresponding coupling products. Using highly active manganese, a variety of… Show more

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Cited by 11 publications
(2 citation statements)
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“…However, low functional group tolerance, poor regioselectivity, and formation of undesired side products have limited these reactions to be employed to their full potential . The nucleophilic addition of organometallic reagents like organozinc , Cd , and Sn to carboxylic acid derivatives is an alternative method that addresses the problems of drastic reaction conditions and low product yields due to the formation of tertiary alcohols. Thus, the development of a mild as well as highly efficient method for the preparation of diaryl ketones has been receiving increasing interest.…”
Section: Introductionmentioning
confidence: 99%
“…However, low functional group tolerance, poor regioselectivity, and formation of undesired side products have limited these reactions to be employed to their full potential . The nucleophilic addition of organometallic reagents like organozinc , Cd , and Sn to carboxylic acid derivatives is an alternative method that addresses the problems of drastic reaction conditions and low product yields due to the formation of tertiary alcohols. Thus, the development of a mild as well as highly efficient method for the preparation of diaryl ketones has been receiving increasing interest.…”
Section: Introductionmentioning
confidence: 99%
“…[3] In this respect, while conventional cross-coupling scenarios that harness the electronically matched reactivity between aryl halides and aryl metallic reagents have oftentimes proved to be applicable, the intrinsic limitations such as restricted availability of pyridyl halides, especially for structurally complicated ones, and low stability of many heterocylic organometallic species have inevitably detracted from its wide applications in complex molecular settings. [4][5][6][7][8] It should also be pointed out is that the situation would become more critical when considering the requirement of site-selective halogenation or metallation with respect to pyridine cores. [9,10] Progress has been made in the development of site-selective CÀH functionalization of pyridines [11] and also synthetic elaborations based on radical type Minisci reactions.…”
mentioning
confidence: 99%