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Literature DB >> 26872072

Copper-Catalyzed SN2'-Selective Allylic Substitution Reaction of gem-Diborylalkanes.

Zhen-Qi Zhang¹, Ben Zhang¹, Xi Lu¹, Jing-Hui Liu¹, Xiao-Yu Lu¹, Bin Xiao¹, Yao Fu¹.

Abstract

A Cu/(NHC)-catalyzed SN2'-selective substitution reaction of allylic electrophiles with gem-diborylalkanes is reported. Different substituted gem-diborylalkanes and allylic electrophiles can be employed in this reaction, and various synthetic valuable functional groups can be tolerated. The asymmetric version of this reaction was initially researched with chiral N-heterocyclic carbene (NHC) ligands.

Entities: Chemical Disease Gene

Year: 2016 PMID： 26872072 DOI： 10.1021/acs.orglett.5b03692

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

7 in total

1. A Boron Alkylidene-Alkene Cycloaddition Reaction: Application to the Synthesis of Aphanamal.

Authors: Xun Liu; T Maxwell Deaton; Fredrik Haeffner; James P Morken
Journal: Angew Chem Int Ed Engl Date: 2017-08-09 Impact factor: 15.336

2. Enantio- and Diastereoselective 1,2-Additions to α-Ketoesters with Diborylmethane and Substituted 1,1-Diborylalkanes.

Authors: Stephanie A Murray; Jacob C Green; Sanita B Tailor; Simon J Meek
Journal: Angew Chem Int Ed Engl Date: 2016-06-20 Impact factor: 15.336

3. Enantio- and Diastereoselective Synthesis of Hydroxy Bis(boronates) via Cu-Catalyzed Tandem Borylation/1,2-Addition.

Authors: Jacob C Green; Matthew V Joannou; Stephanie A Murray; Joseph M Zanghi; Simon J Meek
Journal: ACS Catal Date: 2017-05-25 Impact factor: 13.084

4. Versatile Homoallylic Boronates by Chemo-, S_N 2'-, Diastereo- and Enantioselective Catalytic Sequence of Cu-H Addition to Vinyl-B(pin)/Allylic Substitution.

Authors: Jaehee Lee; Sebastian Torker; Amir H Hoveyda
Journal: Angew Chem Int Ed Engl Date: 2016-12-20 Impact factor: 15.336

Copper-Catalyzed SN2'-Selective Allylic Substitution Reaction of gem-Diborylalkanes.

1. A Boron Alkylidene-Alkene Cycloaddition Reaction: Application to the Synthesis of Aphanamal.

2. Enantio- and Diastereoselective 1,2-Additions to α-Ketoesters with Diborylmethane and Substituted 1,1-Diborylalkanes.

3. Enantio- and Diastereoselective Synthesis of Hydroxy Bis(boronates) via Cu-Catalyzed Tandem Borylation/1,2-Addition.

4. Versatile Homoallylic Boronates by Chemo-, S_N 2'-, Diastereo- and Enantioselective Catalytic Sequence of Cu-H Addition to Vinyl-B(pin)/Allylic Substitution.

5. Enantioselective and site-specific copper-catalyzed reductive allyl-allyl cross-coupling of allenes.

6. Cu-catalyzed cross-coupling reactions of vinyl epoxide with organoboron compounds: access to homoallylic alcohols.

7. Cu-catalyzed C-C bond formation of vinylidene cyclopropanes with carbon nucleophiles.