Computational study of silver-catalyzed stereoselective hydroalkylation of alkynes: Pauli repulsion controlled Z/E selectivity-Reference-Cited by-同舟云学术

Computational study of silver-catalyzed stereoselective hydroalkylation of alkynes: Pauli repulsion controlled Z/E selectivity

Published:2021 Issue: Volume: Page:
ISSN:1359-7345
Container-title:Chemical Communications
language:en
Short-container-title:Chem. Commun.

Author:

Hu Lingfei¹²³⁴⁵,Gao Han¹²³⁴⁵,Hu Yanlei¹²³⁴⁵,Lv Xiangying¹²³⁴⁵^ORCID,Wu Yan-Bo⁶⁷⁸⁹¹⁰^ORCID,Lu Gang¹²³⁴⁵^ORCID

Affiliation:

1. School of Chemistry and Chemical Engineering

2. Key Laboratory of Colloid and Interface Chemistry

3. Ministry of Education

4. Shandong University

5. Jinan

6. Key Lab for Materials of Energy Conversion and Storage of Shanxi Province and Key Lab of Chemical Biology and Molecular Engineering of Ministry of Education

7. Institute of Molecular Science

8. Shanxi University

9. Taiyuan

10. China

Abstract

The σ)(π Pauli repulsion is revealed as the dominant factor affecting the stereoselectivity of 1,2-alkyl migration of alkynyl boronate complexes. This is due to the cationic silver induced unequal redistribution of alkyne π electron density.

Funder

National Natural Science Foundation of China

Natural Science Foundation of Shandong Province

Taishan Scholar Foundation of Shandong Province

Shandong University

Publisher

Royal Society of Chemistry (RSC)

Subject

Materials Chemistry,Metals and Alloys,Surfaces, Coatings and Films,General Chemistry,Ceramics and Composites,Electronic, Optical and Magnetic Materials,Catalysis

Link

http://pubs.rsc.org/en/content/articlepdf/2021/CC/D1CC01917A

Reference43 articles.

1. Copper-Catalyzed Hydroalkylation of Terminal Alkynes

2. Diastereodivergent Reductive Cross Coupling of Alkynes through Tandem Catalysis: Z- and E-Selective Hydroarylation of Terminal Alkynes

3. Stereospecific Synthesis of E-Alkenes through Anti-Markovnikov Hydroalkylation of Terminal Alkynes

4. Palladium‐Catalyzed Formal Hydroalkylation of Aryl‐Substituted Alkynes with Hydrazones

5. Tandem Reactions Enable Trans- and Cis-Hydro-Tertiary-Alkylations Catalyzed by a Copper Salt

Cited by 23 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Origin of site-selectivity of hydrogen atom transfer in carbohydrate C–H alkylations via photoredox catalysis;Organic Chemistry Frontiers;2024

2. Mechanistic Insights into the DABCO-Catalyzed Cloke–Wilson Rearrangement: A DFT Perspective;The Journal of Organic Chemistry;2023-10-27

3. Lewis Acid-Catalyzed Carbonyl-Ene Reaction: Interplay between Aromaticity, Synchronicity, and Pauli Repulsion;The Journal of Organic Chemistry;2023-07-24

4. The Origin of Catalysis and Regioselectivity of Lewis Acid‐Catalyzed Diels‐Alder Reactions with Tropone**;Chemistry – A European Journal;2023-05-19

5. Origins of Regioselectivity in CuH-Catalyzed Hydrofunctionalization of Alkenes;The Journal of Organic Chemistry;2023-02-15