Literature DB >> 28447093

Highly nucleophilic vitamin B12-assisted nickel-catalysed reductive coupling of aryl halides and non-activated alkyl tosylates.

Kimihiro Komeyama1, Ryo Ohata, Shinnosuke Kiguchi, Itaru Osaka.   

Abstract

Reductive cross-coupling of aryl halides with ubiquitous alkyl tosylates was developed using a combination of nickel and vitamin B12 (VB12: cyanocobalamin) catalysts. The tosylate was activated by reduced VB12 to form alkyl cobalt(iii), which served as a good alkylating agent for aryl-nickel species, leading to C(sp3)-C(sp2) bond formation.

Entities:  

Year:  2017        PMID： 28447093     DOI： 10.1039/c7cc01932g

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  10 in total

1.  Mechanistic Interrogation of Co/Ni-Dual Catalyzed Hydroarylation.

Authors:  Sophia L Shevick; Carla Obradors; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2018-09-18       Impact factor: 15.419

2.  Nickel-Catalyzed Alkyl-Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes.

Authors:  Amberly B Sanford; Taylor A Thane; Tristan M McGinnis; Pan-Pan Chen; Xin Hong; Elizabeth R Jarvo
Journal:  J Am Chem Soc       Date:  2020-03-04       Impact factor: 15.419

Review 3.  Homogeneous Organic Electron Donors in Nickel-Catalyzed Reductive Transformations.

Authors:  David J Charboneau; Nilay Hazari; Haotian Huang; Mycah R Uehling; Susan L Zultanski
Journal:  J Org Chem       Date:  2022-06-07       Impact factor: 4.198

4.  Ni-catalyzed cross-electrophile coupling between vinyl/aryl and alkyl sulfonates: synthesis of cycloalkenes and modification of peptides.

Authors:  Jicheng Duan; Yun-Fei Du; Xiaobo Pang; Xing-Zhong Shu
Journal:  Chem Sci       Date:  2019-08-05       Impact factor: 9.825

5.  Cobalt Catalyst Determines Regioselectivity in Ring Opening of Epoxides with Aryl Halides.

Authors:  Aleksandra Potrząsaj; Mateusz Musiejuk; Wojciech Chaładaj; Maciej Giedyk; Dorota Gryko
Journal:  J Am Chem Soc       Date:  2021-06-03       Impact factor: 15.419

6.  Visible light-driven Giese reaction with alkyl tosylates catalysed by nucleophilic cobalt.

Authors:  Kimihiro Komeyama; Takuya Michiyuki; Yoshikazu Teshima; Itaru Osaka
Journal:  RSC Adv       Date:  2021-01-18       Impact factor: 3.361

7.  Cu(ii)-vitamin C-complex catalyzed photo-induced homocoupling reaction of aryl boronic acid in base-free and visible light conditions.

Authors:  Narges Pourmorteza; Maasoumeh Jafarpour; Fahimeh Feizpour; Abdolreza Rezaeifard
Journal:  RSC Adv       Date:  2022-02-08       Impact factor: 3.361

8.  Zinc-Mediated Transformation of 1,3-Diols to Cyclopropanes for Late-Stage Modification of Natural Products and Medicinal Agents.

Authors:  Tristan M McGinnis; Taylor A Thane; Elizabeth R Jarvo
Journal:  Org Lett       Date:  2022-07-22       Impact factor: 6.072

9.  Formate-Mediated Cross-Electrophile Reductive Coupling of Aryl Iodides and Bromopyridines.

Authors:  Leyah A Schwartz; Kim Spielmann; Robert A Swyka; Ming Xiang; Michael J Krische
Journal:  Isr J Chem       Date:  2020-10-15       Impact factor: 3.333

10.  Reductive Cyclization of Unactivated Alkyl Chlorides with Tethered Alkenes under Visible-Light Photoredox Catalysis.

Authors:  Miguel Claros; Felix Ungeheuer; Federico Franco; Vlad Martin-Diaconescu; Alicia Casitas; Julio Lloret-Fillol
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-08       Impact factor: 15.336
  10 in total

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