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Literature DB >> 28371182

Substrate-Assisted, Transition-Metal-Free Diboration of Alkynamides with Mixed Diboron: Regio- and Stereoselective Access to trans-1,2-Vinyldiboronates.

Astha Verma¹, Russell F Snead¹, Yumin Dai¹, Carla Slebodnick¹, Yinuo Yang², Haizhu Yu², Fu Yao³, Webster L Santos¹.

Abstract

A substrate-assisted diboration of alkynamides using the unsymmetrical pinacolato-1,8-diaminonaphthalenato diboron (pinBBdan) is described. The transition-metal-free reaction proceeds in a regio- and stereoselective fashion to exclusively afford trans-vinyldiboronates in good to excellent yields. Notably, Bdan and Bpin are installed on the α- and β-carbon atoms, respectively.

Entities: Chemical

Keywords: alkenes; boron; chemoselectivity; cross-coupling; synthetic methods

Year: 2017 PMID： 28371182 DOI： 10.1002/anie.201700946

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

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Cited

6 in total

1. 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

2. Substrate-Controlled Cu(OAc)₂-Catalyzed Stereoselective Semi-Reduction of Alkynes with MeOH as the Hydrogen Source.

Authors: Jiuzhong Huang; Xiaoning Li; Huiling Wen; Lu Ouyang; Nianhua Luo; Jianhua Liao; Renshi Luo
Journal: ACS Omega Date: 2021-04-22

3. One-Metal/Two-Ligand for Dual Activation Tandem Catalysis: Photoinduced Cu-Catalyzed Anti-hydroboration of Alkynes.

Authors: Javier Corpas; Miguel Gomez-Mendoza; Jonathan Ramírez-Cárdenas; Víctor A de la Peña O'Shea; Pablo Mauleón; Ramón Gómez Arrayás; Juan C Carretero
Journal: J Am Chem Soc Date: 2022-07-05 Impact factor: 16.383

4. Enantioselective Copper-Catalyzed sp²/sp³ Diborylation of 1-Chloro-1-Trifluoromethylalkenes.

Authors: Zhenwei Fan; Mingxing Ye; Yahao Wang; Jian Qiu; Wangyang Li; Xingxing Ma; Kai Yang; Qiuling Song
Journal: ACS Cent Sci Date: 2022-07-20 Impact factor: 18.728

5. 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

6. 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

6 in total

Substrate-Assisted, Transition-Metal-Free Diboration of Alkynamides with Mixed Diboron: Regio- and Stereoselective Access to trans-1,2-Vinyldiboronates.

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

2. Substrate-Controlled Cu(OAc)2-Catalyzed Stereoselective Semi-Reduction of Alkynes with MeOH as the Hydrogen Source.

3. One-Metal/Two-Ligand for Dual Activation Tandem Catalysis: Photoinduced Cu-Catalyzed Anti-hydroboration of Alkynes.

4. Enantioselective Copper-Catalyzed sp2/sp3 Diborylation of 1-Chloro-1-Trifluoromethylalkenes.

5. 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.

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

2. Substrate-Controlled Cu(OAc)₂-Catalyzed Stereoselective Semi-Reduction of Alkynes with MeOH as the Hydrogen Source.

4. Enantioselective Copper-Catalyzed sp²/sp³ Diborylation of 1-Chloro-1-Trifluoromethylalkenes.

5. 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.

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