Literature DB >> 29379940

gem-Diborylalkanes: recent advances in their preparation, transformation and application.

Rajender Nallagonda1, Kishor Padala, Ahmad Masarwa.   

Abstract

Recently, gem-diborylalkanes have attracted much attention as versatile building blocks and fundamental intermediates in organic synthesis, because they enable multiple C-C bond construction and further transformation at C-B bonds. Importantly, gem-diborylalkanes can be utilised as bisnucleophilic partners in a variety of chemo-selective C-C bond-forming reactions. This review describes recent developments in synthesising gem-diborylalkanes in complex molecules along with their chemical transformation. In the first part of the review the different synthetic approaches used to synthesise gem-diborylalkanes are described. In the second part, an overview of the chemoselective transformation of gem-diborylalkanes into various functionalized materials is discussed along with one-carbon homologation of diborylmethane via a selective uni- and bidirectional method.

Entities:  

Year:  2018        PMID: 29379940     DOI: 10.1039/c7ob02978k

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  13 in total

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4.  α-Boryl Organometallic Reagents in Catalytic Asymmetric Synthesis.

Authors:  Chenlong Zhang; Weipeng Hu; James P Morken
Journal:  ACS Catal       Date:  2021-08-12       Impact factor: 13.700

5.  Enantioselective Cu-catalyzed double hydroboration of alkynes to access chiral gem-diborylalkanes.

Authors:  Shengnan Jin; Jinxia Li; Kang Liu; Wei-Yi Ding; Shuai Wang; Xiujuan Huang; Xue Li; Peiyuan Yu; Qiuling Song
Journal:  Nat Commun       Date:  2022-06-20       Impact factor: 17.694

6.  Chemodivergent transformations of amides using gem-diborylalkanes as pro-nucleophiles.

Authors:  Wei Sun; Lu Wang; Yue Hu; Xudong Wu; Chungu Xia; Chao Liu
Journal:  Nat Commun       Date:  2020-06-19       Impact factor: 14.919

7.  1,n-Bisborylalkanes via Radical Boron Migration.

Authors:  Dinghai Wang; Christian Mück-Lichtenfeld; Armido Studer
Journal:  J Am Chem Soc       Date:  2020-05-06       Impact factor: 15.419

8.  A modular and concise approach to MIDA acylboronates via chemoselective oxidation of unsymmetrical geminal diborylalkanes: unlocking access to a novel class of acylborons.

Authors:  Shengjia Lin; Lucia Wang; Negin Aminoleslami; Yanting Lao; Chelsea Yagel; Abhishek Sharma
Journal:  Chem Sci       Date:  2019-03-21       Impact factor: 9.825

9.  Selective Boryl-Anion Migration in a Vinyl sp2 -sp3 Diborane Induced by Soft Borane Lewis Acids.

Authors:  Valerio Fasano; Jessica Cid; Richard J Procter; Emily Ross; Michael J Ingleson
Journal:  Angew Chem Int Ed Engl       Date:  2018-09-10       Impact factor: 15.336

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

Authors:  Jichao Chen; Shang Gao; Ming Chen
Journal:  Chem Sci       Date:  2019-10-09       Impact factor: 9.825

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