Literature DB >> 24283652

Development of an air-stable nickel precatalyst for the amination of aryl chlorides, sulfamates, mesylates, and triflates.

Nathaniel H Park1, Georgiy Teverovskiy, Stephen L Buchwald.   

Abstract

A new air-stable nickel precatalyst for C-N cross-coupling is reported. The developed catalyst system displays a greatly improved substrate scope for C-N bond formation to include both a wide range of aryl and heteroaryl electrophiles and aryl, heteroaryl, and alkylamines. The catalyst system is also compatible with a weak base, allowing the amination of substrates containing base-sensitive functional groups.

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Year:  2013        PMID： 24283652      PMCID： PMC3926134          DOI： 10.1021/ol403209k

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  26 in total

1.  Aromatic Aminations by Heterogeneous Ni(0)/C Catalysis We thank the NIH (GM 40 287) for supporting our programs, and the Sumitomo Chemical Co. Ltd. for a research assistantship awarded to H.U.

Authors:  Bruce H. Lipshutz; Hiroshi Ueda
Journal:  Angew Chem Int Ed Engl       Date:  2000-12-15       Impact factor: 15.336

2.  Nickel-catalyzed asymmetric α-arylation and heteroarylation of ketones with chloroarenes: effect of halide on selectivity, oxidation state, and room-temperature reactions.

Authors:  Shaozhong Ge; John F Hartwig
Journal:  J Am Chem Soc       Date:  2011-09-27       Impact factor: 15.419

3.  trans-Chloro(1-naphthyl)bis(triphenylphosphine)nickel(II)/PCy3 catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates at room temperature.

Authors:  Pawaret Leowanawat; Na Zhang; Mehtap Safi; David J Hoffman; Miriam C Fryberger; Aiswaria George; Virgil Percec
Journal:  J Org Chem       Date:  2012-03-07       Impact factor: 4.354

4.  Pd-catalyzed cross-coupling reactions of amides and aryl mesylates.

Authors:  Karin Dooleweerdt; Brett P Fors; Stephen L Buchwald
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

5.  Arylation of diarylamines catalyzed by Ni(II)-PPh3 system.

Authors:  Chen Chen; Lian-Ming Yang
Journal:  Org Lett       Date:  2005-05-26       Impact factor: 6.005

6.  Nickel-catalyzed amination of aryl phosphates through cleaving aryl C-O bonds.

Authors:  Jin-Hua Huang; Lian-Ming Yang
Journal:  Org Lett       Date:  2011-06-20       Impact factor: 6.005

7.  Nickel-catalyzed C-O activation of phenol derivatives with potassium heteroaryltrifluoroborates.

Authors:  Gary A Molander; Floriane Beaumard
Journal:  Org Lett       Date:  2010-09-17       Impact factor: 6.005

8.  Simplifying nickel(0) catalysis: an air-stable nickel precatalyst for the internally selective benzylation of terminal alkenes.

Authors:  Eric A Standley; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2013-01-14       Impact factor: 15.419

9.  Nickel-catalyzed cross-coupling of diarylamines with haloarenes.

Authors:  Cai-Yan Gao; Xingbo Cao; Lian-Ming Yang
Journal:  Org Biomol Chem       Date:  2009-08-03       Impact factor: 3.876

10.  Efficient nickel-mediated intramolecular amination of aryl chlorides.

Authors:  Rafik Omar-Amrani; Antoine Thomas; Eric Brenner; Raphaël Schneider; Yves Fort
Journal:  Org Lett       Date:  2003-06-26       Impact factor: 6.005
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  23 in total

1.  Breaking Amides using Nickel Catalysis.

Authors:  Jacob E Dander; Neil K Garg
Journal:  ACS Catal       Date:  2017-01-06       Impact factor: 13.084

2.  Well-defined nickel and palladium precatalysts for cross-coupling.

Authors:  Nilay Hazari; Patrick R Melvin; Megan Mohadjer Beromi
Journal:  Nat Rev Chem       Date:  2017-03-01       Impact factor: 34.035

3.  Electrochemically Enabled, Nickel-Catalyzed Amination.

Authors:  Chao Li; Yu Kawamata; Hugh Nakamura; Julien C Vantourout; Zhiqing Liu; Qinglong Hou; Denghui Bao; Jeremy T Starr; Jinshan Chen; Ming Yan; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-14       Impact factor: 15.336

4.  Mechanism and Origins of Ligand-Controlled Stereoselectivity of Ni-Catalyzed Suzuki-Miyaura Coupling with Benzylic Esters: A Computational Study.

Authors:  Shuo-Qing Zhang; Buck L H Taylor; Chong-Lei Ji; Yuan Gao; Michael R Harris; Luke E Hanna; Elizabeth R Jarvo; K N Houk; Xin Hong
Journal:  J Am Chem Soc       Date:  2017-09-07       Impact factor: 15.419

5.  Modifications to the Aryl Group of dppf-Ligated Ni σ‑Aryl Precatalysts: Impact on Speciation and Catalytic Activity in Suzuki-Miyaura Coupling Reactions.

Authors:  Megan Mohadjer Beromi; Gourab Banerjee; Gary W Brudvig; David J Charboneau; Nilay Hazari; Hannah M C Lant; Brandon Q Mercado
Journal:  Organometallics       Date:  2018-10-16       Impact factor: 3.876

6.  Stable, Well-Defined Nickel(0) Catalysts for Catalytic C-C and C-N Bond Formation.

Authors:  Alex J Nett; Santiago Cañellas; Yuki Higuchi; Michael T Robo; Jeanne M Kochkodan; M Taylor Haynes; Jeff W Kampf; John Montgomery
Journal:  ACS Catal       Date:  2018-06-11       Impact factor: 13.084

7.  Benchtop Delivery of Ni(cod)2 using Paraffin Capsules.

Authors:  Jacob E Dander; Nicholas A Weires; Neil K Garg
Journal:  Org Lett       Date:  2016-07-25       Impact factor: 6.005

8.  Nanonickel-catalyzed Suzuki-Miyaura cross-couplings in water.

Authors:  Sachin Handa; Eric D Slack; Bruce H Lipshutz
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-25       Impact factor: 15.336

9.  Aryl amination using ligand-free Ni(II) salts and photoredox catalysis.

Authors:  Emily B Corcoran; Michael T Pirnot; Shishi Lin; Spencer D Dreher; Daniel A DiRocco; Ian W Davies; Stephen L Buchwald; David W C MacMillan
Journal:  Science       Date:  2016-06-23       Impact factor: 47.728

10.  Ni-Catalyzed Enantioselective C-Acylation of α-Substituted Lactams.

Authors:  Masaki Hayashi; Shoshana Bachman; Satoshi Hashimoto; Chad C Eichman; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2016-07-15       Impact factor: 15.419
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