Literature DB >> 21842839

[3+2] coupling of quinone monoacetals by combined acid-hydrogen bond donor.

Toshifumi Dohi1, Yinjun Hu, Tohru Kamitanaka, Naohiko Washimi, Yasuyuki Kita.   

Abstract

The expeditious and efficient [3+2] coupling approach of quinone monoacetals 1 with alkene nucleophiles 2 by the action of an activated Brønsted acid in the presence of a hydrogen bond donor perfluorinated alcohol has been achieved. With the optimized combined acid, the reaction could proceed under mild conditions by only mixing the two reactants to afford the cycloadducts 3 in a short time (within 10 min) with good to quantitative yields.
© 2011 American Chemical Society

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Year:  2011        PMID: 21842839     DOI: 10.1021/ol201886r

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  Synthesis of o-chlorophenols via an unexpected nucleophilic chlorination of quinone monoketals mediated by N,N'-dimethylhydrazine dihydrochloride.

Authors:  Zhiwei Yin; Jinzhu Zhang; Jing Wu; Riana Green; Sihan Li; Shengping Zheng
Journal:  Org Biomol Chem       Date:  2014-05-14       Impact factor: 3.876

2.  An efficient and expeditious synthesis of novel 2,2-dialkyl-2,3-dihydrobenzofurans from phenols and 2,2-dialkylacetaldehydes.

Authors:  Amitabh Jha; Ting-Yi Chou; Doug Vaughan
Journal:  Mol Divers       Date:  2013-03-07       Impact factor: 2.943

3.  Nucleophilic Arylation of Halopurines Facilitated by Brønsted Acid in Fluoroalcohol.

Authors:  Naoko Takenaga; Toshitaka Shoji; Takayuki Menjo; Akiko Hirai; Shohei Ueda; Kotaro Kikushima; Tomonori Hanasaki; Toshifumi Dohi
Journal:  Molecules       Date:  2019-10-23       Impact factor: 4.411

  3 in total

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