Literature DB >> 25711834

Engaging nonaromatic, heterocyclic tosylates in reductive cross-coupling with aryl and heteroaryl bromides.

Gary A Molander1, Kaitlin M Traister, Brian T O'Neill.   

Abstract

A method has been developed for the introduction of nonaromatic heterocyclic structures onto aryl and heteroaryl bromides using alkyl tosylates in a reductive cross-coupling manifold. This protocol offers an improvement over previous methods by utilizing alkyl tosylate coupling partners that are bench-stable, crystalline solids that can be prepared from inexpensive, commercially available alcohols.

Entities:  

Year:  2015        PMID： 25711834     DOI： 10.1021/acs.joc.5b00135

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  19 in total

1.  Reductive Decarboxylative Alkynylation of N-Hydroxyphthalimide Esters with Bromoalkynes.

Authors:  Liangbin Huang; Astrid M Olivares; Daniel J Weix
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-17       Impact factor: 15.336

2.  Cross-Electrophile Coupling of Unactivated Alkyl Chlorides.

Authors:  Holt A Sakai; Wei Liu; Chi Chip Le; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2020-06-26       Impact factor: 15.419

3.  Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions.

Authors:  Kelsey E Poremba; Sara E Dibrell; Sarah E Reisman
Journal:  ACS Catal       Date:  2020-06-24       Impact factor: 13.084

4.  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

5.  Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C-N Bond Activation.

Authors:  Corey H Basch; Jennie Liao; Jianyu Xu; Jacob J Piane; Mary P Watson
Journal:  J Am Chem Soc       Date:  2017-04-05       Impact factor: 15.419

6.  Deaminative Reductive Cross-Electrophile Couplings of Alkylpyridinium Salts and Aryl Bromides.

Authors:  Jennie Liao; Corey H Basch; Megan E Hoerrner; Michael R Talley; Brian P Boscoe; Joseph W Tucker; Michelle R Garnsey; Mary P Watson
Journal:  Org Lett       Date:  2019-03-27       Impact factor: 6.005

7.  Alcohols as Latent Coupling Fragments for Metallaphotoredox Catalysis: sp3-sp2 Cross-Coupling of Oxalates with Aryl Halides.

Authors:  Xiaheng Zhang; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2016-10-17       Impact factor: 15.419

8.  In-Situ Bromination Enables Formal Cross-Electrophile Coupling of Alcohols with Aryl and Alkenyl Halides.

Authors:  Benjamin K Chi; Jonas K Widness; Michael M Gilbert; Daniel C Salgueiro; Kevin J Garcia; Daniel J Weix
Journal:  ACS Catal       Date:  2021-12-21       Impact factor: 13.084

9.  Nickel-Catalyzed Asymmetric Reductive Cross-Coupling between Heteroaryl Iodides and α-Chloronitriles.

Authors:  Nathaniel T Kadunce; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2015-08-13       Impact factor: 15.419

10.  Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Chlorides with Primary Alkyl Chlorides.

Authors:  Seoyoung Kim; Matthew J Goldfogel; Michael M Gilbert; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2020-05-21       Impact factor: 15.419
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