Literature DB >> 26564784

Synthesis of 1,1-Diborylalkenes through a Brønsted Base Catalyzed Reaction between Terminal Alkynes and Bis(pinacolato)diboron.

Akira Morinaga1, Kazunori Nagao1, Hirohisa Ohmiya2, Masaya Sawamura3.   

Abstract

A method for the synthesis of 1,1-diborylalkenes through a Brønsted base catalyzed reaction between terminal alkynes and bis(pinacolato)diboron has been developed. The procedure allows direct synthesis of functionalized 1,1-diborylalkenes from various terminal alkynes including propiolates, propiolamides, and 2-ethynylazoles.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Brønsted bases; boration; diborylalkenes; organocatalysis; synthetic methods

Year:  2015        PMID： 26564784     DOI： 10.1002/anie.201509218

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  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.  Catalytic Enantioselective Synthesis of 1,4-Keto-Alkenylboronate Esters and 1,4-Dicarbonyls.

Authors:  Michael Z Liang; Simon J Meek
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-23       Impact factor: 15.336

3.  Synthesis of Stereodefined 1,1-Diborylalkenes via Copper-Catalyzed Diboration of Terminal Alkynes.

Authors:  Yang Gao; Zhong-Qian Wu; Keary M Engle
Journal:  Org Lett       Date:  2020-06-23       Impact factor: 6.005

4.  Organobase-catalyzed 1,1-diborylation of terminal alkynes under metal-free conditions.

Authors:  Junchen Li; Min An; Zhenhua Gao; Yongbiao Guo; Haibo Liu; Peichao Zhao; Xiaojing Bi; Enxue Shi; Junhua Xiao
Journal:  RSC Adv       Date:  2022-06-01       Impact factor: 4.036

5.  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

6.  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

7.  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

8.  Synthesis of 1,1-Diboryl Alkenes Using the Boryl-Heck Reaction.

Authors:  Olamide O Idowu; Jacob C Hayes; William B Reid; Donald A Watson
Journal:  Org Lett       Date:  2021-05-27       Impact factor: 6.072

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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