ICl‐Induced Intramolecular Electrophilic Cyclization of 1‐[4′‐Methoxy(1,1′‐biphenyl)2‐yl]alkynones—A Facile Approach to Spiroconjugated Molecules

Chen, Yu; Liu, Xiaochen; Lee, Min Wook; Huang, Chenlong; Inoyatov, Igor; Chen, Zhiwei; Perl, Abraham C.; Hersh, William H.

doi:10.1002/chem.201301582

Cited by 41 publications

(19 citation statements)

References 30 publications

(9 reference statements)

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“…Through this methodology, many useful functional groups could be successfully introduced into organic frameworks. Nevertheless, up to date, only few strategies have been developed to construct substituted spirocyclohexadienones via the difunctionalization of alkynes such as ipso -carbohalogenation, carbothiocyanation, carboalkylation, carboacylation, and carbonphosphonation. , It is still a challenging but attractive task to develop direct, convenient, efficient, and environmentally benign reaction system to afford a variety of important and structurally diverse functional spirocyclohexadienones.…”

Section: Introductionmentioning

confidence: 99%

Metal-Free Oxidative Spirocyclization of Alkynes with Sulfonylhydrazides Leading to 3-Sulfonated Azaspiro[4,5]trienones

et al. 2015

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A novel and direct oxidative spirocyclization of arylpropiolamides with sulfonylhydrazides leading to 3-sulfonated azaspiro[4,5]trienones has been developed under metal-free conditions. The reaction is performed in a tandem manner constituted by the sequential sulfonylation of alkynes, ipso-carbocyclization, dearomatization, hydration, and oxidation processes, providing a convenient and efficient approach to various sulfonated azaspiro[4,5] trienones of biological importance.

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Section: Introductionmentioning

confidence: 99%

Metal-Free Oxidative Spirocyclization of Alkynes with Sulfonylhydrazides Leading to 3-Sulfonated Azaspiro[4,5]trienones

et al. 2015

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“…[11] The desired spiroconjugated products 29 were generatedv ia a6 -endo-dig pathway in up to 99 %y ield under mild conditions. [11] The desired spiroconjugated products 29 were generatedv ia a6 -endo-dig pathway in up to 99 %y ield under mild conditions.…”

Section: Alkynesmentioning

confidence: 99%

“…Chen and co‐workers investigated the possibility of employing 1‐[4′‐methoxy(1,1′‐biphenyl)‐2‐yl]alkynones 28 in a similar dearomatizing iodocyclization reaction . The desired spiroconjugated products 29 were generated via a 6‐ endo ‐ dig pathway in up to 99 % yield under mild conditions.…”

Section: Halogenation At Alkynes or Alkenesmentioning

confidence: 99%

Dearomatization through Halofunctionalization Reactions

Liang

Zheng

You

2016

Chemistry A European J

147

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Recent advances in dearomatization through halofunctionalization reactions are summarized in this Minireview. Two general categories of strategies are currently employed in this field. On one hand, the reaction can be initiated with electrophilic halogenation at an alkyne or alkene moiety. The resulting halonium ion intermediate is then captured by a pendant aromatic ring at the ipso position, affording the dearomatization product. On the other hand, electrophilic halogenation can directly take place at a substituted arene, and the final dearomatization product is furnished by deprotonation or intramolecular nucleophilic trap. Highly enantioselective variants have been realized in the latter case by organocatalysis or transition metal catalysis. By applying these methods, various valuable halogenated polycyclic molecular architectures have been obtained from readily available starting materials.

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“…Chen andc o-workersi nvestigated the possibility of employing 1-[4'-methoxy(1,1'-biphenyl)-2-yl]alkynones 28 in as imilar dearomatizing iodocyclization reaction. [11] The desired spiroconjugated products 29 were generatedv ia a6 -endo-dig pathway in up to 99 %y ield under mild conditions. Interestingly,i n some cases, the 7-endo-dig cyclization also occurred as ac ompetitiver eaction pathway,l eadingt o5 H-dibenzo[a,c] [7]annulen-5-ones 30 (Scheme 9).…”

Section: Alkynesmentioning

confidence: 99%