Literature DB >> 23828735

Catalytic Aminohalogenation of Alkenes and Alkynes.

Sherry R Chemler1, Michael T Bovino.   

Abstract

Catalytic aminohalogenation methods enable the regio- and stereoselective vicinal difunctionalization of n class="Chemical">alkynes, allenes and alkenes with amine and halogen moieties. A range of protocols and reaction mechanisms including organometallic, Lewis base, Lewis acid and Brønsted acid catalysis have been disclosed, enabling the regio- and stereoselective synthesis of halogen-functionalized acyclic amines and nitrogen heterocycles. Recent advances including aminofluorination and catalytic enantioselective aminohalogenation reactions are summarized in this review.

Entities:  

Keywords:  alkenes; alkynes; allenes; aminohalogenation; catalysis; enantioselelective; haloamidation; haloamines

Year:  2013        PMID: 23828735      PMCID: PMC3697159          DOI: 10.1021/cs4001249

Source DB:  PubMed          Journal:  ACS Catal            Impact factor:   13.084


  33 in total

1.  Ionic liquid media resulted in the first asymmetric aminohalogenation reaction of alkenes.

Authors:  Xin Xu; S R S Saibabu Kotti; Junying Liu; John F Cannon; Allan D Headley; Guigen Li
Journal:  Org Lett       Date:  2004-12-23       Impact factor: 6.005

2.  Catalytic asymmetric chloroamination reaction of α,β-unsaturated γ-keto esters and chalcones.

Authors:  Yunfei Cai; Xiaohua Liu; Jun Jiang; Weiliang Chen; Lili Lin; Xiaoming Feng
Journal:  J Am Chem Soc       Date:  2011-03-28       Impact factor: 15.419

3.  Palladium-catalyzed intermolecular aminofluorination of styrenes.

Authors:  Shuifa Qiu; Tao Xu; Juan Zhou; Yinlong Guo; Guosheng Liu
Journal:  J Am Chem Soc       Date:  2010-03-10       Impact factor: 15.419

Review 4.  Catalytic, asymmetric halofunctionalization of alkenes--a critical perspective.

Authors:  Scott E Denmark; William E Kuester; Matthew T Burk
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-25       Impact factor: 15.336

5.  Enantioselective bromoaminocyclization using amino-thiocarbamate catalysts.

Authors:  Ling Zhou; Jie Chen; Chong Kiat Tan; Ying-Yeung Yeung
Journal:  J Am Chem Soc       Date:  2011-05-03       Impact factor: 15.419

6.  Copper-catalyzed aminobromination/elimination process: an efficient access to alpha,beta-unsaturated vicinal haloamino ketones and esters.

Authors:  Hao Sun; Guangqian Zhang; Sanjun Zhi; Jianlin Han; Guigen Li; Yi Pan
Journal:  Org Biomol Chem       Date:  2010-08-13       Impact factor: 3.876

7.  C2-symmetric cyclic selenium-catalyzed enantioselective bromoaminocyclization.

Authors:  Feng Chen; Chong Kiat Tan; Ying-Yeung Yeung
Journal:  J Am Chem Soc       Date:  2013-01-17       Impact factor: 15.419

8.  Virantmycin, a new antiviral antibiotic produced by a strain of Streptomyces.

Authors:  A Nakagawa; Y Iwai; H Hashimoto; N Miyazaki; R Oiwa; Y Takahashi; A Hirano; N Shibukawa; Y Kojima; S Omura
Journal:  J Antibiot (Tokyo)       Date:  1981-11       Impact factor: 2.649

9.  Lewis basic selenium catalyzed chloroamidation of olefins using nitriles as the nucleophiles.

Authors:  Daniel Weiliang Tay; Ivan Tan Tsoi; Jun Cheng Er; Gulice Yiu Chung Leung; Ying-Yeung Yeung
Journal:  Org Lett       Date:  2013-03-05       Impact factor: 6.005

10.  Transition metal-catalyzed regio- and stereoselective aminobromination of olefins with TsNH2 and NBS as nitrogen and bromine sources.

Authors:  Vinay V Thakur; Siva Kumar Talluri; A Sudalai
Journal:  Org Lett       Date:  2003-03-20       Impact factor: 6.005

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  29 in total

1.  Catalytic Regio- and Enantioselective Haloazidation of Allylic Alcohols.

Authors:  Frederick J Seidl; Chang Min; Jovan A Lopez; Noah Z Burns
Journal:  J Am Chem Soc       Date:  2018-11-12       Impact factor: 15.419

2.  Copper-Catalyzed 1,2-Aminocyanation of Unactivated Alkenes via Cyano Migration.

Authors:  Yungeun Kwon; Qiu Wang
Journal:  Org Lett       Date:  2020-05-08       Impact factor: 6.005

3.  Intramolecular aminocyanation of alkenes by N-CN bond cleavage.

Authors:  Zhongda Pan; Sarah M Pound; Naveen R Rondla; Christopher J Douglas
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-09       Impact factor: 15.336

4.  Highly Stereoselective Intermolecular Haloetherification and Haloesterification of Allyl Amides.

Authors:  Bardia Soltanzadeh; Arvind Jaganathan; Richard J Staples; Babak Borhan
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-25       Impact factor: 15.336

5.  Iron(II)-Catalyzed Intermolecular Aminofluorination of Unfunctionalized Olefins Using Fluoride Ion.

Authors:  Deng-Fu Lu; Cheng-Liang Zhu; Jeffrey D Sears; Hao Xu
Journal:  J Am Chem Soc       Date:  2016-08-26       Impact factor: 15.419

6.  Concise Synthesis and Antimicrobial Evaluation of the Guanidinium Alkaloid Batzelladine D: Development of a Stereodivergent Strategy.

Authors:  You-Chen Lin; Aubert Ribaucourt; Yasamin Moazami; Joshua G Pierce
Journal:  J Am Chem Soc       Date:  2020-05-12       Impact factor: 15.419

Review 7.  Catalytic, Stereoselective Dihalogenation of Alkenes: Challenges and Opportunities.

Authors:  Alexander J Cresswell; Stanley T-C Eey; Scott E Denmark
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-02       Impact factor: 15.336

8.  Vicinal, Double C-H Functionalization of Alcohols via an Imidate Radical-Polar Crossover Cascade.

Authors:  Allen F Prusinowski; Raymond K Twumasi; Ethan A Wappes; David A Nagib
Journal:  J Am Chem Soc       Date:  2020-03-06       Impact factor: 15.419

Review 9.  Stereoselective Halogenation in Natural Product Synthesis.

Authors:  Won-jin Chung; Christopher D Vanderwal
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-02       Impact factor: 15.336

10.  Nanostructured Iron Sulfide/N, S Dual-Doped Carbon Nanotube-Graphene Composites as Efficient Electrocatalysts for Oxygen Reduction Reaction.

Authors:  Gyu Sik Chae; Duck Hyun Youn; Jae Sung Lee
Journal:  Materials (Basel)       Date:  2021-04-23       Impact factor: 3.623

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