Literature DB >> 28074601

Boraformylation and Silaformylation of Allenes.

Tetsuaki Fujihara1, Ayumi Sawada1, Tatsuya Yamaguchi1, Yosuke Tani1,2, Jun Terao1,3, Yasushi Tsuji1.   

Abstract

The boraformylation of allenes with B2 (pin)2 and a formate ester as boron and formyl source, respectively, proceeds in the presence of a copper catalyst. The reaction selectively affords the corresponding β-boryl β,γ-unsaturated aldehydes in good to high yields. Furthermore, the silaformylation of allenes was achieved with a formate ester and PhMe2 Si-B(pin) as the silicon source.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  allenes; borylation; copper; formate esters; silylation

Year:  2017        PMID： 28074601     DOI： 10.1002/anie.201611314

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


  11 in total

1.  Multifaceted Substrate-Ligand Interactions Promote the Copper-Catalyzed Hydroboration of Benzylidenecyclobutanes and Related Compounds.

Authors:  Taeho Kang; Tuğçe G Erbay; Kane L Xu; Gary M Gallego; Alexander Burtea; Sajiv K Nair; Ryan L Patman; Ru Zhou; Scott C Sutton; Indrawan J McAlpine; Peng Liu; Keary M Engle
Journal:  ACS Catal       Date:  2020-10-27       Impact factor: 13.084

2.  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

3.  Streamlined Catalytic Enantioselective Synthesis of α-Substituted β,γ-Unsaturated Ketones and Either of the Corresponding Tertiary Homoallylic Alcohol Diastereomers.

Authors:  Juan Del Pozo; Shaochen Zhang; Filippo Romiti; Shibo Xu; Ryan P Conger; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2020-10-05       Impact factor: 15.419

Review 4.  Enantioselective copper catalysed, direct functionalisation of allenes via allyl copper intermediates.

Authors:  Alexander P Pulis; Kay Yeung; David J Procter
Journal:  Chem Sci       Date:  2017-06-08       Impact factor: 9.825

5.  α-Silicon effect assisted Curtin-Hammett allylation using allylcopper reagents derived from 1,3-dienylsilanes.

Authors:  Shang Gao; Ming Chen
Journal:  Chem Sci       Date:  2019-06-28       Impact factor: 9.825

6.  Catalytic Lewis Base Additive Enables Selective Copper-Catalyzed Borylative α-C-H Allylation of Alicyclic Amines.

Authors:  Borja Pérez-Saavedra; Álvaro Velasco-Rubio; Eva Rivera-Chao; Jesús A Varela; Carlos Saá; Martín Fañanás-Mastral
Journal:  J Am Chem Soc       Date:  2022-08-24       Impact factor: 16.383

7.  C-Boron Enolates Enable Palladium Catalyzed Carboboration of Internal 1,3-Enynes.

Authors:  Ziyong Wang; Jason Wu; Walid Lamine; Bo Li; Jean-Marc Sotiropoulos; Anna Chrostowska; Karinne Miqueu; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-31       Impact factor: 16.823

8.  Cu-catalyzed enantioselective synthesis of tertiary benzylic copper complexes and their in situ addition to carbonyl compounds.

Authors:  Fengchang Cheng; Wenxin Lu; Wei Huang; Lu Wen; Mingfeng Li; Fanke Meng
Journal:  Chem Sci       Date:  2018-04-30       Impact factor: 9.825

9.  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.  Catalytic enantioselective allene-anhydride approach to β,γ-unsaturated enones bearing an α-all-carbon-quarternary center.

Authors:  Yuan Yuan; Xue Zhang; Hui Qian; Shengming Ma
Journal:  Chem Sci       Date:  2020-07-22       Impact factor: 9.825
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