Electron deficient bonding of benzoheterocycles to triosmium clusters: synthesis and applications to organic chemistry

Abedin, Md. Joynal; Bergman, Brian; Holmquist, Richard; Smith, Ryan; Rosenberg, Edward; Ciurash, Joana; Hardcastle, Kenneth I.; Roe, Jay; Vazquez, Vanessa; Roe, Candace; Kabir, Shariff E.; Roy, B. K.; Alam, Shahana; Azam, Kazi A.

doi:10.1016/s0010-8545(99)00154-x

“…The known methods include intramolecular cyclization of benzenoids, naphthalenoids, stilbenoids and biphenyloids, intermolecular cyclization/cycloaddition of benzenoids and naphthalenoids, as well as ring expansion/contraction reactions . Similarly, benzoquinolines were synthesized by inter-/intramolecular cyclization involving 1-aminonaphthalene, dehydrogenation of N-heterocycles, photocyclization of 3-styrylpyridines/stilbenes, intramolecular cyclization of tetralone derived acylazide, inter-/intramolecular cyclization of biaryls, and rearrangements . The only report on the synthesis of 2-aminophenanthrenes is based on benzannulation of an alkyne without any metal catalyst …”

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confidence: 99%

Synthesis of Aminophenanthrenes and Benzoquinolines via Hauser–Kraus Annulation of Sulfonyl Phthalide with Rauhut–Currier Adducts of Nitroalkenes

Kumar

¹

,

Mane

²

,

Namboothiri

³

2017

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The Hauser-Kraus reaction of sulfonyl phthalide with nitroalkene derivatives provides access to aminophenanthrenes, including phenanthrene-substituted amino acids and benzoquinolines. The intermediate quinones bearing a key ketoalkyl moiety undergoes facile intramolecular enamine cyclization. Interestingly, enamines derived from primary and secondary amines undergo cyclization via C-centered nucleophilic attack to provide aminophenanthrenes, whereas those derived from ammonia undergo cyclization via N-centered nucleophilic attack leading to benzoquinolines. A one-pot protocol for the direct transformation of phthalides and nitroalkene derivatives to aminophenanthrenes and benzoquinolines has also been developed.

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Mechanisms of Reaction of Organometallic Complexes

Atwood

¹

,

Rosenberg

²

2005

Encyclopedia of Inorganic Chemistry

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An overview of the mechanistic features of organometallic reactions is presented. The primary mechanistic types discussed are ligand substitution, oxidative addition, reductive elimination, and electron transfer. Each reaction pathway is discussed within the context of the common electron counts encountered for most organometallic complexes. Examples of how these common reaction pathways extend to polynuclear complexes are also presented. Although reasonable generalizations with regard to overall reaction rates and stepwise mechanisms using the electron count formalism can be made, many recent reports point out that the details of ligand and metal center structure can override these general trends. A considerable amount of quantitative rate data is provided and computational methodologies for understanding the observed rates are discussed.

show abstract

Mechanisms of Reaction of Organometallic Complexes

Atwood

¹

,

Rosenberg

²

2005

Encyclopedia of Inorganic and Bioinorganic Chemistry

View full text Add to dashboard Cite

An overview of the mechanistic features of organometallic reactions is presented. The primary mechanistic types discussed are ligand substitution, oxidative addition, reductive elimination, and electron transfer. Each reaction pathway is discussed within the context of the common electron counts encountered for most organometallic complexes. Examples of how these common reaction pathways extend to polynuclear complexes are also presented. Although reasonable generalizations with regard to overall reaction rates and stepwise mechanisms using the electron count formalism can be made, many recent reports point out that the details of ligand and metal center structure can override these general trends. A considerable amount of quantitative rate data is provided and computational methodologies for understanding the observed rates are discussed.

show abstract

Electron deficient bonding of benzoheterocycles to triosmium clusters: synthesis and applications to organic chemistry

Cited by 49 publications

References 22 publications

Synthesis of Aminophenanthrenes and Benzoquinolines via Hauser–Kraus Annulation of Sulfonyl Phthalide with Rauhut–Currier Adducts of Nitroalkenes

Synthesis of Aminophenanthrenes and Benzoquinolines via Hauser–Kraus Annulation of Sulfonyl Phthalide with Rauhut–Currier Adducts of Nitroalkenes

Mechanisms of Reaction of Organometallic Complexes

Mechanisms of Reaction of Organometallic Complexes

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