Literature DB >> 22369478

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.

Pawaret Leowanawat1, Na Zhang, Mehtap Safi, David J Hoffman, Miriam C Fryberger, Aiswaria George, Virgil Percec.   

Abstract

trans-Chloro(1-naphthyl)bis(triphenylphosphine)nickel(II) complex/PCy(3) system has been successfully applied as catalyst for the Suzuki-Miyaura cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature. This cross-coupling reaction tolerates various functional groups, including keto, imino, ester, ether, and cyano. Together with the nickel-catalyzed, one-pot, two-step neopentylglycolborylation, this bench stable and inexpensive Ni(II)-based catalyst can be utilized as an alternative to Ni(COD)(2)/PCy(3) to provide an inexpensive, robust, and convenient synthesis of biaryl and heterobiaryl compounds.

Entities:  

Year:  2012        PMID: 22369478     DOI: 10.1021/jo3001194

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  12 in total

1.  Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis.

Authors:  Timothy B Boit; Ana S Bulger; Jacob E Dander; Neil K Garg
Journal:  ACS Catal       Date:  2020-09-10       Impact factor: 13.084

2.  Mechanistic Study of an Improved Ni Precatalyst for Suzuki-Miyaura Reactions of Aryl Sulfamates: Understanding the Role of Ni(I) Species.

Authors:  Megan Mohadjer Beromi; Ainara Nova; David Balcells; Ann M Brasacchio; Gary W Brudvig; Louise M Guard; Nilay Hazari; David J Vinyard
Journal:  J Am Chem Soc       Date:  2017-01-10       Impact factor: 15.419

3.  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

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.  Pd-Catalyzed Suzuki-Miyaura and Hiyama-Denmark Couplings of Aryl Sulfamates.

Authors:  Patrick R Melvin; Nilay Hazari; Megan Mohadjer Beromi; Hemali P Shah; Michael J Williams
Journal:  Org Lett       Date:  2016-11-03       Impact factor: 6.005

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

Authors:  Nathaniel H Park; Georgiy Teverovskiy; Stephen L Buchwald
Journal:  Org Lett       Date:  2013-11-27       Impact factor: 6.005

8.  Nickel-Catalyzed Stille Cross Coupling of C-O Electrophiles.

Authors:  John E A Russell; Emily D Entz; Ian M Joyce; Sharon R Neufeldt
Journal:  ACS Catal       Date:  2019-03-04       Impact factor: 13.084

9.  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

10.  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

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