Literature DB >> 28165185

Construction of Nine-Membered Heterocycles through Palladium-Catalyzed Formal [5+4] Cycloaddition.

Li-Cheng Yang1, Zi-Qiang Rong1, Ya-Nong Wang1, Zher Yin Tan1, Min Wang1, Yu Zhao1.   

Abstract

The first catalytic formal [5+4] cycloaddition to prepare nine-membered heterocycles is presented. Under palladium catalysis, the reaction of N-tosyl azadienes and substituted vinylethylene carbonates (VECs) proceeds smoothly to produce benzofuran-fused heterocycles in uniformly high efficiency. Highly diastereoselective functionalization of the nine-membered heterocycles through peripheral attack is also demonstrated.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  [5+4] cycloaddition; heterocycles; homogeneous catalysis; nine-membered rings; palladium

Year:  2017        PMID： 28165185     DOI： 10.1002/anie.201611474

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  7 in total

1.  Access to benzo-fused nine-membered heterocyclic alkenes with a trifluoromethyl carbinol moiety via a double decarboxylative formal ring-expansion process under palladium catalysis.

Authors:  Pulakesh Das; Satoshi Gondo; Punna Nagender; Hiroto Uno; Etsuko Tokunaga; Norio Shibata
Journal:  Chem Sci       Date:  2018-02-23       Impact factor: 9.825

Review 2.  Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization.

Authors:  Mickael Choury; Alexandra Basilio Lopes; Gaëlle Blond; Mihaela Gulea
Journal:  Molecules       Date:  2020-07-09       Impact factor: 4.411

3.  Palladium nanoparticles as efficient catalyst for C-S bond formation reactions.

Authors:  Mei-Na Zhang; Shahid Khan; Junjie Zhang; Ajmal Khan
Journal:  RSC Adv       Date:  2020-08-21       Impact factor: 4.036

4.  Construction of azaheterocycles via Pd-catalyzed migratory cycloannulation reaction of unactivated alkenes.

Authors:  Jin-Ping Wang; Shuo Song; Yichen Wu; Peng Wang
Journal:  Nat Commun       Date:  2022-08-27       Impact factor: 17.694

5.  Access to substituted cyclobutenes by tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition of dipropargylphosphonates under Ag/Co relay catalysis.

Authors:  Qijian Ni; Xiaoxiao Song; Chin Wen Png; Yongliang Zhang; Yu Zhao
Journal:  Chem Sci       Date:  2020-10-16       Impact factor: 9.825

6.  Nickel-catalyzed asymmetric reductive aryl-allylation of unactivated alkenes.

Authors:  Zhiyang Lin; Youxiang Jin; Weitao Hu; Chuan Wang
Journal:  Chem Sci       Date:  2021-04-09       Impact factor: 9.825

7.  A remote C-C bond cleavage-enabled skeletal reorganization: Access to medium-/large-sized cyclic alkenes.

Authors:  Lei Li; Zhong-Liang Li; Qiang-Shuai Gu; Na Wang; Xin-Yuan Liu
Journal:  Sci Adv       Date:  2017-11-03       Impact factor: 14.136
  7 in total

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