Literature DB >> 31030508

Hydroalkylation of Olefins To Form Quaternary Carbons.

Samantha A Green1, Tucker R Huffman1, Ruairí O McCourt1, Vincent van der Puyl1, Ryan A Shenvi1.   

Abstract

Metal-hydride hydrogen atom transfer (MHAT) functionalizes alkenes with predictable branched (Markovnikov) selectivity. The breadth of these transformations has been confined to π-radical traps; no sp3 electrophiles have been reported. Here we describe a Mn/Ni dual catalytic system that hydroalkylates unactivated olefins with unactivated alkyl halides, yielding aliphatic quaternary carbons.

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Year:  2019        PMID： 31030508      PMCID： PMC8923049          DOI： 10.1021/jacs.9b02844

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


  48 in total

1.  Quaternary Centers by Nickel-Catalyzed Cross-Coupling of Tertiary Carboxylic Acids and (Hetero)Aryl Zinc Reagents.

Authors:  Tie-Gen Chen; Haolin Zhang; Pavel K Mykhailiuk; Rohan R Merchant; Courtney A Smith; Tian Qin; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-30       Impact factor: 15.336

2.  Iron(III)/NaBH4-mediated additions to unactivated alkenes: synthesis of novel 20'-vinblastine analogues.

Authors:  Erick K Leggans; Timothy J Barker; Katharine K Duncan; Dale L Boger
Journal:  Org Lett       Date:  2012-02-28       Impact factor: 6.005

3.  Formation of C(sp(3) )-C(sp(3) ) Bonds through Nickel-Catalyzed Decarboxylative Olefin Hydroalkylation Reactions.

Authors:  Xi Lu; Bin Xiao; Lei Liu; Yao Fu
Journal:  Chemistry       Date:  2016-07-04       Impact factor: 5.236

4.  Nickel-Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms.

Authors:  Tian Qin; Lara R Malins; Jacob T Edwards; Rohan R Merchant; Alexander J E Novak; Jacob Z Zhong; Riley B Mills; Ming Yan; Changxia Yuan; Martin D Eastgate; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-16       Impact factor: 15.336

5.  Nickel-Catalyzed Reductive Allylation of Tertiary Alkyl Halides with Allylic Carbonates.

Authors:  Haifeng Chen; Xiao Jia; Yingying Yu; Qun Qian; Hegui Gong
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-12       Impact factor: 15.336

6.  Synthesis of the Privileged 8-Arylmenthol Class by Radical Arylation of Isopulegol.

Authors:  Steven W M Crossley; Ruben M Martinez; Sebastián Guevara-Zuluaga; Ryan A Shenvi
Journal:  Org Lett       Date:  2016-05-13       Impact factor: 6.005

7.  Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins.

Authors:  Steven W M Crossley; Carla Obradors; Ruben M Martinez; Ryan A Shenvi
Journal:  Chem Rev       Date:  2016-07-27       Impact factor: 60.622

Review 8.  Recent advances in homogeneous nickel catalysis.

Authors:  Sarah Z Tasker; Eric A Standley; Timothy F Jamison
Journal:  Nature       Date:  2014-05-15       Impact factor: 49.962

9.  Iron-Nickel Dual-Catalysis: A New Engine for Olefin Functionalization and the Formation of Quaternary Centers.

Authors:  Samantha A Green; Suhelen Vásquez-Céspedes; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2018-07-26       Impact factor: 15.419

10.  A practical and catalytic reductive olefin coupling.

Authors:  Julian C Lo; Yuki Yabe; Phil S Baran
Journal:  J Am Chem Soc       Date:  2014-01-15       Impact factor: 15.419
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  16 in total

1.  Role of Electron-Deficient Olefin Ligands in a Ni-Catalyzed Aziridine Cross-Coupling To Generate Quaternary Carbons.

Authors:  Jesús G Estrada; Wendy L Williams; Stephen I Ting; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2020-04-29       Impact factor: 15.419

2.  Electroreductive Carbofunctionalization of Alkenes with Alkyl Bromides via a Radical-Polar Crossover Mechanism.

Authors:  Wen Zhang; Song Lin
Journal:  J Am Chem Soc       Date:  2020-11-24       Impact factor: 15.419

3.  Nickel-Catalyzed Dicarbofunctionalization of Alkenes.

Authors:  Xiaoxu Qi; Tianning Diao
Journal:  ACS Catal       Date:  2020-07-02       Impact factor: 13.084

4.  A biomimetic SH2 cross-coupling mechanism for quaternary sp3-carbon formation.

Authors:  Wei Liu; Marissa N Lavagnino; Colin A Gould; Jesús Alcázar; David W C MacMillan
Journal:  Science       Date:  2021-11-11       Impact factor: 47.728

5.  Nickel-Catalyzed C(sp3)-C(sp3) Cross-Electrophile Coupling of In Situ Generated NHP Esters with Unactivated Alkyl Bromides.

Authors:  Kai Kang; Daniel J Weix
Journal:  Org Lett       Date:  2022-04-13       Impact factor: 6.072

6.  On the Nature of C(sp3)-C(sp2) Bond Formation in Nickel-Catalyzed Tertiary Radical Cross-Couplings: A Case Study of Ni/Photoredox Catalytic Cross-Coupling of Alkyl Radicals and Aryl Halides.

Authors:  Mingbin Yuan; Zhihui Song; Shorouk O Badir; Gary A Molander; Osvaldo Gutierrez
Journal:  J Am Chem Soc       Date:  2020-04-01       Impact factor: 15.419

7.  Site-Specific Alkene Hydromethylation via Protonolysis of Titanacyclobutanes.

Authors:  James A Law; Noah M Bartfield; James H Frederich
Journal:  Angew Chem Int Ed Engl       Date:  2021-05-19       Impact factor: 16.823

8.  A Giese reaction for electron-rich alkenes.

Authors:  Qi Huang; Sankar Rao Suravarapu; Philippe Renaud
Journal:  Chem Sci       Date:  2020-12-17       Impact factor: 9.825

9.  Construction of congested Csp3-Csp3 bonds by a formal Ni-catalyzed alkylboration.

Authors:  Amit Kumar Simlandy; Stephen R Sardini; M Kevin Brown
Journal:  Chem Sci       Date:  2021-03-09       Impact factor: 9.825

Review 10.  Methodologies for the synthesis of quaternary carbon centers via hydroalkylation of unactivated olefins: twenty years of advances.

Authors:  Thiago S Silva; Fernando Coelho
Journal:  Beilstein J Org Chem       Date:  2021-07-07       Impact factor: 2.883
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