Literature DB >> 34278397

Recent advances in palladium-catalyzed (hetero)annulation of C[double bond, length as m-dash]C bonds with ambiphilic organo(pseudo)halides.

Hui-Qi Ni1, Phillippa Cooper1, Keary M Engle1.   

Abstract

Palladium has proven to be effective in catalyzing the (hetero)annulation of C[double bond, length as m-dash]C bonds with ambiphilic organo(pseudo)halides. Through the employment of appropriate ambiphilic coupling partners, efficient annulation of a variety of allenes, 1,3-dienes, strained alkenes, styrenes, and other C[double bond, length as m-dash]C bond variants can be achieved to provide direct access to numerous useful hetero- and carbocyclic scaffolds. In this Feature Article, we summarize palladium-catalyzed (hetero)annulation methods reported since 2005 (spanning just over 15 years) and discuss outstanding challenges in this area of study.

Entities:  

Year:  2021        PMID： 34278397      PMCID： PMC8364377          DOI： 10.1039/d1cc02836g

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.065


  44 in total

1.  Synthesis and antiproliferative activity of 6-naphthylpterocarpans.

Authors:  Ádám Szappanos; Attila Mándi; Katalin Gulácsi; Erika Lisztes; Balázs István Tóth; Tamás Bíró; Sándor Antus; Tibor Kurtán
Journal:  Org Biomol Chem       Date:  2020-03-05       Impact factor: 3.876

2.  Palladium-catalyzed enantioselective carboannulation of 1,3-dienes with aryl iodides enables access to chiral indanes.

Authors:  Xiang Wu; Shu-Sen Chen; Ling Zhang; Hai-Jun Wang; Liu-Zhu Gong
Journal:  Chem Commun (Camb)       Date:  2018-08-23       Impact factor: 6.222

3.  Palladium-catalyzed intermolecular [4 + 2] formal cycloaddition with (Z)-3-iodo allylic nucleophiles and allenamides.

Authors:  Fachao Yan; Hanbing Liang; Bing Ai; Wenjing Liang; Luyang Jiao; Shuzhi Yao; Pingping Zhao; Qing Liu; Yunhui Dong; Hui Liu
Journal:  Org Biomol Chem       Date:  2019-03-06       Impact factor: 3.876

4.  Palladium-Catalyzed Cascade sp2 C-H Functionalization/Intramolecular Asymmetric Allylation: From Aryl Ureas and 1,3-Dienes to Chiral Indolines.

Authors:  Shu-Sen Chen; Min-Song Wu; Zhi-Yong Han
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-03       Impact factor: 15.336

5.  Pd(II)-Catalyzed Asymmetric Oxidative Annulation of N-Alkoxyheteroaryl Amides and 1,3-Dienes.

Authors:  Tao Zhang; Hong-Cheng Shen; Jia-Cheng Xu; Tao Fan; Zhi-Yong Han; Liu-Zhu Gong
Journal:  Org Lett       Date:  2019-03-22       Impact factor: 6.005

6.  Synthesis of spiroindanes by palladium-catalyzed oxidative annulation of non- or weakly activated 1,3-dienes involving C-H functionalization.

Authors:  Imtiaz Khan; Suresh Reddy Chidipudi; Hon Wai Lam
Journal:  Chem Commun (Camb)       Date:  2015-02-14       Impact factor: 6.222

7.  Probing the mechanism of the Heck reaction with arene diazonium salts by electrospray mass and tandem mass spectrometry.

Authors:  Adão A Sabino; Angelo H L Machado; Carlos Roque D Correia; Marcos N Eberlin
Journal:  Angew Chem Int Ed Engl       Date:  2004-05-03       Impact factor: 15.336

8.  An elimination/Heck coupling/allylation cascade reaction: synthesis of 2,3-dihydrobenzofurans from allenoate adducts.

Authors:  Jianguo Yang; Hanjie Mo; Haijian Wu; Dongdong Cao; Chengmin Pan; Zhiming Wang
Journal:  Chem Commun (Camb)       Date:  2018-01-31       Impact factor: 6.222

9.  Vinylogous Elimination/Heck Coupling/Allylation Domino Reactions: Access to 2-Substituted 2,3-Dihydrobenzofurans and Indolines.

Authors:  Jianguo Yang; Hanjie Mo; Xiuxiu Jin; Dongdong Cao; Haijian Wu; Di Chen; Zhiming Wang
Journal:  J Org Chem       Date:  2018-02-22       Impact factor: 4.354

10.  Trapping the Lewis acid generated transient species from pentafulvene derived diazanorbornenes with ortho-functionalized aryl iodides and aliphatic alcohols.

Authors:  S Sarath Chand; S Saranya; P Preethanuj; B P Dhanya; E Jijy; Praveen Prakash; B S Sasidhar; Jan Szymoniak; P V Santhini; K V Radhakrishnan
Journal:  Org Biomol Chem       Date:  2014-05-21       Impact factor: 3.876
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  3 in total

1.  Mapping Ambiphile Reactivity Trends in the Anti-(Hetero)annulation of Non-Conjugated Alkenes via PdII /PdIV Catalysis.

Authors:  Hui-Qi Ni; Phillippa Cooper; Shouliang Yang; Fen Wang; Neal Sach; Pranali G Bedekar; Joyann S Donaldson; Michelle Tran-Dubé; Indrawan J McAlpine; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-02       Impact factor: 15.336

2.  Convergent Synthesis of Dihydrobenzofurans via Urea Ligand-Enabled Heteroannulation of 2-Bromophenols with 1,3-Dienes.

Authors:  Kaitlyn E Houghtling; Amanda M Canfield; Shauna M Paradine
Journal:  Org Lett       Date:  2022-07-29       Impact factor: 6.072

3.  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
  3 in total

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