Literature DB >> 25469703

Copper-catalyzed regiodivergent silacarboxylation of allenes with carbon dioxide and a silylborane.

Yosuke Tani1, Tetsuaki Fujihara, Jun Terao, Yasushi Tsuji.   

Abstract

A regiodivergent silacarboxylation of allenes under a CO2 atmosphere with PhMe2Si-B(pin) as a silicon source in the presence of a copper catalyst at 70 °C has been developed. The regioselectivity of the reaction is successfully reversed by the proper choice of ligand; carboxylated vinylsilanes are obtained with rac-Me-DuPhos as the ligand, whereas the use of PCy3 affords carboxylated allylsilanes. Thus, two different carboxylated silanes can be selectively and regiodivergently synthesized from a single allene substrate.

Entities:  

Year:  2014        PMID： 25469703     DOI： 10.1021/ja512040c

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


  10 in total

1.  NHC Ligands Tailored for Simultaneous Regio- and Enantiocontrol in Nickel-Catalyzed Reductive Couplings.

Authors:  Hengbin Wang; Gang Lu; Grant J Sormunen; Hasnain A Malik; Peng Liu; John Montgomery
Journal:  J Am Chem Soc       Date:  2017-07-03       Impact factor: 15.419

2.  Exo-selective reductive macrocyclization of ynals.

Authors:  Hengbin Wang; Solymar Negretti; Allison R Knauff; John Montgomery
Journal:  Org Lett       Date:  2015-03-06       Impact factor: 6.005

3.  Synthesis of Secondary and Tertiary Alkylboranes via Formal Hydroboration of Terminal and 1,1-Disubstituted Alkenes.

Authors:  Hilary A Kerchner; John Montgomery
Journal:  Org Lett       Date:  2016-10-27       Impact factor: 6.005

4.  Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination.

Authors:  Thomas J O'Connor; Binh Khanh Mai; Jordan Nafie; Peng Liu; F Dean Toste
Journal:  J Am Chem Soc       Date:  2021-08-16       Impact factor: 16.383

5.  Catalyst-controlled regiodivergent ring-opening C(sp3)-Si bond-forming reactions of 2-arylaziridines with silylborane enabled by synergistic palladium/copper dual catalysis.

Authors:  Youhei Takeda; Kaoru Shibuta; Shohei Aoki; Norimitsu Tohnai; Satoshi Minakata
Journal:  Chem Sci       Date:  2019-07-31       Impact factor: 9.825

Review 6.  Recent advances in Cu-catalyzed C(sp3)-Si and C(sp3)-B bond formation.

Authors:  Balaram S Takale; Ruchita R Thakore; Elham Etemadi-Davan; Bruce H Lipshutz
Journal:  Beilstein J Org Chem       Date:  2020-04-15       Impact factor: 2.883

7.  Synthesis of 1,4,5,6-tetrahydropyridazines and pyridazines via transition-metal-free (4 + 2) cycloaddition of alkoxyallenes with 1,2-diaza-1,3-dienes.

Authors:  Qi Wu; Pan-Lin Shao; Yun He
Journal:  RSC Adv       Date:  2019-07-10       Impact factor: 4.036

8.  Catalyst-free carbosilylation of alkenes using silyl boronates and organic fluorides via selective C-F bond activation.

Authors:  Jun Zhou; Bingyao Jiang; Yamato Fujihira; Zhengyu Zhao; Takanori Imai; Norio Shibata
Journal:  Nat Commun       Date:  2021-06-18       Impact factor: 14.919

9.  Copper-Catalyzed Borylative Cross-Coupling of Allenes and Imines: Selective Three-Component Assembly of Branched Homoallyl Amines.

Authors:  James Rae; Kay Yeung; Joseph J W McDouall; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-03       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
  10 in total

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