Literature DB >> 24847909

Trans-diborylation of alkynes: pseudo-intramolecular strategy utilizing a propargylic alcohol unit.

Yuki Nagashima1, Keiichi Hirano, Ryo Takita, Masanobu Uchiyama.   

Abstract

We present the first trans-selective diborylation reaction of alkynes. By means of theoretical calculation-assisted reaction analysis, we designed a pseudo-intramolecular reaction of diboron, propargyl alcohol, and a base to facilitate B-B bond activation and C-B bond formation with high efficiency. This approach provides synthetically versatile and densely functionalized 4-borylated 1,2-oxaborol-2(5H)-oles (vinyldiboronates) in a straightforward manner. Detailed computational analysis showed that the directing alkoxide functionality markedly lowers the activation energy of B-C bond formation.

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Year:  2014        PMID： 24847909     DOI： 10.1021/ja5036754

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  10 in total

1.  Cobalt-Catalyzed 1,1-Diboration of Terminal Alkynes: Scope, Mechanism, and Synthetic Applications.

Authors:  Simon Krautwald; Máté J Bezdek; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2017-03-01       Impact factor: 15.419

2.  Synthesis of oxaboranes via nickel-catalyzed dearylative cyclocondensation.

Authors:  Mason T Koeritz; Haley K Banovetz; Sean A Prell; Levi M Stanley
Journal:  Chem Sci       Date:  2022-05-20       Impact factor: 9.969

3.  Mechanism of NHC-Catalyzed Conjugate Additions of Diboron and Borosilane Reagents to α,β-Unsaturated Carbonyl Compounds.

Authors:  Hao Wu; Jeannette M Garcia; Fredrik Haeffner; Suttipol Radomkit; Adil R Zhugralin; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2015-08-11       Impact factor: 15.419

4.  Reactivity of highly Lewis acidic diborane(4) towards pyridine and isocyanide: formation of boraalkene-pyridine complex and ortho-functionalized pyridine derivatives.

Authors:  Yuhei Katsuma; Hiroki Asakawa; Makoto Yamashita
Journal:  Chem Sci       Date:  2017-12-11       Impact factor: 9.825

5.  Regio- and Stereoselective Synthesis of 1,1-Diborylalkenes via Brønsted Base-Catalyzed Mixed Diboration of Alkynyl Esters and Amides with BpinBdan.

Authors:  Xiaocui Liu; Wenbo Ming; Xiaoling Luo; Alexandra Friedrich; Jan Maier; Udo Radius; Webster L Santos; Todd B Marder
Journal:  European J Org Chem       Date:  2020-03-18

6.  Mechanistic study on the reaction of pinB-BMes2 with alkynes based on experimental investigation and DFT calculations: gradual change of mechanism depending on the substituent.

Authors:  Linlin Wu; Chiemi Kojima; Ka-Ho Lee; Shogo Morisako; Zhenyang Lin; Makoto Yamashita
Journal:  Chem Sci       Date:  2021-06-17       Impact factor: 9.825

7.  Hydroxyl-directed stereoselective diboration of alkenes.

Authors:  Thomas P Blaisdell; Thomas C Caya; Liang Zhang; Amparo Sanz-Marco; James P Morken
Journal:  J Am Chem Soc       Date:  2014-06-24       Impact factor: 15.419

8.  Transition-Metal-Free Borylation of Allylic and Propargylic Alcohols.

Authors:  Núria Miralles; Rauful Alam; Kálmán J Szabó; Elena Fernández
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-02       Impact factor: 15.336

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.  Copper-Catalyzed Triboration of Terminal Alkynes Using B2 pin2 : Efficient Synthesis of 1,1,2-Triborylalkenes.

Authors:  Xiaocui Liu; Wenbo Ming; Alexandra Friedrich; Florian Kerner; Todd B Marder
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-19       Impact factor: 15.336
  10 in total

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