Literature DB >> 22849697

Nickel-catalyzed amination of aryl sulfamates and carbamates using an air-stable precatalyst.

Liana Hie1, Stephen D Ramgren, Tehetena Mesganaw, Neil K Garg.   

Abstract

A facile nickel-catalyzed method to achieve the amination of synthetically useful aryl sulfamates and carbamates is reported. Contrary to most Ni-catalyzed amination reactions, this user-friendly approach relies on an air-stable Ni(II) precatalyst, which, when employed with a mild reducing agent, efficiently delivers aminated products in good to excellent yields. The scope of the method is broad with respect to both coupling partners and includes heterocyclic substrates.

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Year:  2012        PMID： 22849697      PMCID： PMC3427767          DOI： 10.1021/ol301847m

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


  35 in total

1.  Directed ortho borylation of phenol derivatives catalyzed by a silica-supported iridium complex.

Authors:  Kenji Yamazaki; Soichiro Kawamorita; Hirohisa Ohmiya; Masaya Sawamura
Journal:  Org Lett       Date:  2010-09-17       Impact factor: 6.005

2.  A synthetic double punch: Suzuki-Miyaura cross-coupling mates with C-H functionalization.

Authors:  Christiane E I Knappke; Axel Jacobi von Wangelin
Journal:  Angew Chem Int Ed Engl       Date:  2010-05-10       Impact factor: 15.336

3.  Palladium-catalyzed ortho-arylation of O-phenylcarbamates with simple arenes and sodium persulfate.

Authors:  Xiaodan Zhao; Charles S Yeung; Vy M Dong
Journal:  J Am Chem Soc       Date:  2010-04-28       Impact factor: 15.419

4.  Ni(COD)2/PCy3 catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature.

Authors:  Pawaret Leowanawat; Na Zhang; Ana-Maria Resmerita; Brad M Rosen; Virgil Percec
Journal:  J Org Chem       Date:  2011-11-16       Impact factor: 4.354

5.  Rhodium-catalyzed direct ortho C-H olefination of phenol derivatives.

Authors:  Chao Feng; Teck-Peng Loh
Journal:  Chem Commun (Camb)       Date:  2011-08-18       Impact factor: 6.222

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.  Palladium-catalysed ortho-arylation of carbamate-protected phenols.

Authors:  Robin B Bedford; Ruth L Webster; Charlotte J Mitchell
Journal:  Org Biomol Chem       Date:  2009-09-30       Impact factor: 3.876

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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  14 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.  Breaking Amides using Nickel Catalysis.

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

3.  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

4.  A modular, air-stable nickel precatalyst.

Authors:  Jason D Shields; Erin E Gray; Abigail G Doyle
Journal:  Org Lett       Date:  2015-04-17       Impact factor: 6.005

5.  Nickel-catalyzed amination of aryl chlorides with ammonia or ammonium salts.

Authors:  Rebecca A Green; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-25       Impact factor: 15.336

6.  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

7.  Nickel-catalyzed Suzuki-Miyaura couplings in green solvents.

Authors:  Stephen D Ramgren; Liana Hie; Yuxuan Ye; Neil K Garg
Journal:  Org Lett       Date:  2013-07-23       Impact factor: 6.005

8.  Bright Side of Lignin Depolymerization: Toward New Platform Chemicals.

Authors:  Zhuohua Sun; Bálint Fridrich; Alessandra de Santi; Saravanakumar Elangovan; Katalin Barta
Journal:  Chem Rev       Date:  2018-01-16       Impact factor: 60.622

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.  Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling in a Green Alcohol Solvent for an Undergraduate Organic Chemistry Laboratory.

Authors:  Liana Hie; Jonah J Chang; Neil K Garg
Journal:  J Chem Educ       Date:  2015-03-10       Impact factor: 2.979
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