Literature DB >> 23879392

Nickel-catalyzed Suzuki-Miyaura couplings in green solvents.

Stephen D Ramgren1, Liana Hie, Yuxuan Ye, Neil K Garg.   

Abstract

The nickel-catalyzed Suzuki-Miyaura coupling of aryl halides and phenol-derived substrates with aryl boronic acids using green solvents, such as 2-Me-THF and tert-amyl alcohol, is reported. This methodology employs the commercially available and air-stable precatalyst, NiCl2(PCy3)2, and gives biaryl products in synthetically useful to excellent yields. Using this protocol, bis(heterocyclic) frameworks can be assembled efficiently.

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Year:  2013        PMID： 23879392      PMCID： PMC3768281          DOI： 10.1021/ol401727y

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


  38 in total

1.  Aryl-aryl bond formation one century after the discovery of the Ullmann reaction.

Authors:  Jwanro Hassan; Marc Sévignon; Christel Gozzi; Emmanuelle Schulz; Marc Lemaire
Journal:  Chem Rev       Date:  2002-05       Impact factor: 60.622

Review 2.  Selected patented cross-coupling reaction technologies.

Authors:  Jean-Pierre Corbet; Gérard Mignani
Journal:  Chem Rev       Date:  2006-07       Impact factor: 60.622

3.  Cross-coupling of aryl/alkenyl pivalates with organozinc reagents through nickel-catalyzed C-O bond activation under mild reaction conditions.

Authors:  Bi-Jie Li; Yi-Zhou Li; Xing-Yu Lu; Jia Liu; Bing-Tao Guan; Zhang-Jie Shi
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Nickel-catalyzed Suzuki-Miyaura coupling of heteroaryl ethers with arylboronic acids.

Authors:  Xiao-Jian Li; Jin-Ling Zhang; Yu Geng; Zhong Jin
Journal:  J Org Chem       Date:  2013-05-08       Impact factor: 4.354

5.  A versatile catalyst system for Suzuki-Miyaura cross-coupling reactions of C(sp(2))-tosylates and mesylates.

Authors:  Brijesh Bhayana; Brett P Fors; Stephen L Buchwald
Journal:  Org Lett       Date:  2009-09-03       Impact factor: 6.005

6.  Suzuki-Miyaura cross-coupling of aryl carbamates and sulfamates: experimental and computational studies.

Authors:  Kyle W Quasdorf; Aurora Antoft-Finch; Peng Liu; Amanda L Silberstein; Anna Komaromi; Tom Blackburn; Stephen D Ramgren; K N Houk; Victor Snieckus; Neil K Garg
Journal:  J Am Chem Soc       Date:  2011-04-01       Impact factor: 15.419

7.  Comparison of arylboron-based nucleophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling with aryl mesylates and sulfamates.

Authors:  Na Zhang; David J Hoffman; Nicholas Gutsche; Jayesh Gupta; Virgil Percec
Journal:  J Org Chem       Date:  2012-06-29       Impact factor: 4.354

8.  N,N-diethyl O-carbamate: directed metalation group and orthogonal Suzuki-Miyaura cross-coupling partner.

Authors:  Aurora Antoft-Finch; Tom Blackburn; Victor Snieckus
Journal:  J Am Chem Soc       Date:  2009-12-16       Impact factor: 15.419

9.  Nickel-catalyzed cross-coupling of aryl methyl ethers with aryl boronic esters.

Authors:  Mamoru Tobisu; Toshiaki Shimasaki; Naoto Chatani
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

10.  Cross-coupling reactions of aryl pivalates with boronic acids.

Authors:  Kyle W Quasdorf; Xia Tian; Neil K Garg
Journal:  J Am Chem Soc       Date:  2008-10-08       Impact factor: 15.419
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  17 in total

1.  DFT Investigation of Suzuki-Miyaura Reactions with Aryl Sulfamates Using a Dialkylbiarylphosphine-Ligated Palladium Catalyst.

Authors:  Patrick R Melvin; Ainara Nova; David Balcells; Nilay Hazari; Mats Tilset
Journal:  Organometallics       Date:  2017-09-13       Impact factor: 3.876

2.  Breaking Amides using Nickel Catalysis.

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

3.  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

4.  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

5.  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

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.  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

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

Review 9.  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

10.  Sulfonamide Synthesis via Calcium Triflimide Activation of Sulfonyl Fluorides.

Authors:  Paramita Mukherjee; Cristian P Woroch; Leah Cleary; Mark Rusznak; Ryan W Franzese; Matthew R Reese; Joseph W Tucker; John M Humphrey; Sarah M Etuk; Sabrina C Kwan; Christopher W Am Ende; Nicholas D Ball
Journal:  Org Lett       Date:  2018-06-11       Impact factor: 6.072
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