Literature DB >> 27846504

Metal-catalyzed reductive coupling of olefin-derived nucleophiles: Reinventing carbonyl addition.

Khoa D Nguyen1, Boyoung Y Park1, Tom Luong1, Hiroki Sato1, Victoria J Garza1, Michael J Krische2.   

Abstract

α-Olefins are the most abundant petrochemical feedstock beyond alkanes, yet their use in commodity chemical manufacture is largely focused on polymerization and hydroformylation. The development of byproduct-free catalytic C-C bond-forming reactions that convert olefins to value-added products remains an important objective. Here, we review catalytic intermolecular reductive couplings of unactivated and activated olefin-derived nucleophiles with carbonyl partners. These processes represent an alternative to the longstanding use of stoichiometric organometallic reagents in carbonyl addition.
Copyright © 2016, American Association for the Advancement of Science.

Entities:  

Year:  2016        PMID： 27846504      PMCID： PMC5130112          DOI： 10.1126/science.aah5133

Source DB:  PubMed          Journal:  Science        ISSN： 0036-8075            Impact factor:   47.728


  42 in total

1.  A New catalytic C[bond]C bond-forming hydrogenation: reductive coupling of dienes and glyoxals under catalytic hydrogenation conditions.

Authors:  Hye-Young Jang; Ryan R Huddleston; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2003-09-05       Impact factor: 15.336

2.  Regio- and diastereoselective C-C coupling of α-olefins and styrenes to 3-hydroxy-2-oxindoles by Ru-catalyzed hydrohydroxyalkylation.

Authors:  Eiji Yamaguchi; Jeffrey Mowat; Tom Luong; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-05       Impact factor: 15.336

3.  Unlocking Hydrogenation for C-C Bond Formation: A Brief Overview of Enantioselective Methods.

Authors:  Abbas Hassan; Michael J Krische
Journal:  Org Process Res Dev       Date:  2011-11-18       Impact factor: 3.317

4.  Paraformaldehyde and methanol as C1  feedstocks in metal-catalyzed C-C couplings of π-unsaturated reactants: beyond hydroformylation.

Authors:  Brannon Sam; Bernhard Breit; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2014-11-27       Impact factor: 15.336

5.  Intermolecular asymmetric reductive aldol reaction of ketones as acceptors promoted by chiral Rh(Phebox) catalyst.

Authors:  Takushi Shiomi; Hisao Nishiyama
Journal:  Org Lett       Date:  2007-03-27       Impact factor: 6.005

6.  Asymmetric reductive coupling of dienes and aldehydes catalyzed by nickel complexes of spiro phosphoramidites: highly enantioselective synthesis of chiral bishomoallylic alcohols.

Authors:  Yun Yang; Shou-Fei Zhu; Hai-Feng Duan; Chang-Yue Zhou; Li-Xin Wang; Qi-Lin Zhou
Journal:  J Am Chem Soc       Date:  2007-02-02       Impact factor: 15.419

7.  Ruthenium-catalyzed C-C bond forming transfer hydrogenation: carbonyl allylation from the alcohol or aldehyde oxidation level employing acyclic 1,3-dienes as surrogates to preformed allyl metal reagents.

Authors:  Fumitoshi Shibahara; John F Bower; Michael J Krische
Journal:  J Am Chem Soc       Date:  2008-04-29       Impact factor: 15.419

8.  Direct, redox-neutral prenylation and geranylation of secondary carbinol C-H bonds: C4-regioselectivity in ruthenium-catalyzed C-C couplings of dienes to α-hydroxy esters.

Authors:  Joyce C Leung; Laina M Geary; Te-Yu Chen; Jason R Zbieg; Michael J Krische
Journal:  J Am Chem Soc       Date:  2012-09-17       Impact factor: 15.419

9.  C═N-containing azaarenes as activating groups in enantioselective catalysis.

Authors:  Daniel Best; Hon Wai Lam
Journal:  J Org Chem       Date:  2014-02-07       Impact factor: 4.354

10.  Ruthenium-catalyzed hydrohydroxyalkylation of acrylates with diols and α-hydroxycarbonyl compounds to form spiro- and α-methylene-γ-butyrolactones.

Authors:  Emma L McInturff; Jeffrey Mowat; Andrew R Waldeck; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-11-05       Impact factor: 15.419
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  61 in total

Review 1.  Engaging Aldehydes in CuH-Catalyzed Reductive Coupling Reactions: Stereoselective Allylation with Unactivated 1,3-Diene Pronucleophiles.

Authors:  Chengxi Li; Kwangmin Shin; Richard Y Liu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-22       Impact factor: 15.336

2.  Inversion of Enantioselectivity in Allene Gas versus Allyl Acetate Reductive Aldehyde Allylation Guided by Metal-Centered Stereogenicity: An Experimental and Computational Study.

Authors:  Seung Wook Kim; Cole C Meyer; Binh Khanh Mai; Peng Liu; Michael J Krische
Journal:  ACS Catal       Date:  2019-09-11       Impact factor: 13.084

3.  A Radical Approach to Anionic Chemistry: Synthesis of Ketones, Alcohols, and Amines.

Authors:  Shengyang Ni; Natalia M Padial; Cian Kingston; Julien C Vantourout; Daniel C Schmitt; Jacob T Edwards; Monika M Kruszyk; Rohan R Merchant; Pavel K Mykhailiuk; Brittany B Sanchez; Shouliang Yang; Matthew A Perry; Gary M Gallego; James J Mousseau; Michael R Collins; Robert J Cherney; Pavlo S Lebed; Jason S Chen; Tian Qin; Phil S Baran
Journal:  J Am Chem Soc       Date:  2019-04-16       Impact factor: 15.419

4.  2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones.

Authors:  Kangnan Li; Xinxin Shao; Luke Tseng; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2018-01-04       Impact factor: 15.419

5.  Carbonyl anti-(α-Amino)allylation via Ruthenium Catalyzed Hydrogen Autotransfer: Use of an Acetylenic Pyrrole as an Allylmetal Pronucleophile.

Authors:  Wandi Zhang; Weijie Chen; Hongde Xiao; Michael J Krische
Journal:  Org Lett       Date:  2017-08-29       Impact factor: 6.005

6.  Enantioselective Iridium-Catalyzed Phthalide Formation through Internal Redox Allylation of Phthalaldehydes.

Authors:  James M Cabrera; Johannes Tauber; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-04       Impact factor: 15.336

7.  CuH-Catalyzed Olefin Functionalization: From Hydroamination to Carbonyl Addition.

Authors:  Richard Y Liu; Stephen L Buchwald
Journal:  Acc Chem Res       Date:  2020-05-13       Impact factor: 22.384

8.  Branch-Selective Addition of Unactivated Olefins into Imines and Aldehydes.

Authors:  Jeishla L M Matos; Suhelen Vásquez-Céspedes; Jieyu Gu; Takuya Oguma; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2018-11-29       Impact factor: 15.419

9.  Reductive C-C Coupling via Hydrogenation and Transfer Hydrogenation: Departure from Stoichiometric Metals in Carbonyl Addition.

Authors:  James Roane; Michael Holmes; Michael J Krische
Journal:  Curr Opin Green Sustain Chem       Date:  2017-06-09

10.  Thermal Hetero-Diels-Alder Reaction of Benzocyclobutenones with Isatins To Form 2-Oxindole Spirolactones.

Authors:  Thomas Wurm; Ben W H Turnbull; Brett R Ambler; Michael J Krische
Journal:  J Org Chem       Date:  2017-11-22       Impact factor: 4.354
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