Literature DB >> 21739947

Highly selective reactions of unbiased alkenyl halides and alkylzinc halides: Negishi-Plus couplings.

Arkady Krasovskiy1, Bruce H Lipshutz.   

Abstract

High yielding stereo- and chemoselective Pd-catalyzed cross-couplings in THF at room temperature of alkenyl iodides and bromides with primary and secondary alkyl zinc iodides have been developed with the aid of N-methyimidazole as the key additive.
© 2011 American Chemical Society

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Year:  2011        PMID： 21739947      PMCID： PMC3365517          DOI： 10.1021/ol201307y

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


  9 in total

1.  Negishi cross-coupling of secondary alkylzinc halides with aryl/heteroaryl halides using Pd-PEPPSI-IPent.

Authors:  Selçuk Çalimsiz; Michael G Organ
Journal:  Chem Commun (Camb)       Date:  2011-02-01       Impact factor: 6.222

2.  New air-stable catalysts for general and efficient suzuki-miyaura cross-coupling reactions of heteroaryl chlorides.

Authors:  Anil S Guram; Anthony O King; John G Allen; Xianghong Wang; Laurie B Schenkel; Johann Chan; Emilio E Bunel; Margaret M Faul; Robert D Larsen; Michael J Martinelli; Paul J Reider
Journal:  Org Lett       Date:  2006-04-27       Impact factor: 6.005

3.  Highly selective reactions of unbiased alkenyl halides and alkylzinc halides: Negishi-Plus couplings.

Authors:  Arkady Krasovskiy; Bruce H Lipshutz
Journal:  Org Lett       Date:  2011-07-08       Impact factor: 6.005

4.  Evidence for the role of tetramethylethylenediamine in aqueous Negishi cross-coupling: synthesis of nonproteinogenic phenylalanine derivatives on water.

Authors:  Andrew J Ross; Frank Dreiocker; Mathias Schäfer; Jos Oomens; Anthony J H M Meijer; Barry T Pickup; Richard F W Jackson
Journal:  J Org Chem       Date:  2011-02-14       Impact factor: 4.354

5.  Stereoselective preparation of functionalized acyclic alkenylmagnesium reagents using i-PrMgCl.LiCl.

Authors:  Hongjun Ren; Arkady Krasovskiy; Paul Knochel
Journal:  Org Lett       Date:  2004-11-11       Impact factor: 6.005

6.  Negishi coupling of secondary alkylzinc halides with aryl bromides and chlorides.

Authors:  Chong Han; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-06-10       Impact factor: 15.419

7.  Density functional theory investigation of the alkyl-alkyl Negishi cross-coupling reaction catalyzed by N-heterocyclic carbene (NHC)-Pd complexes.

Authors:  Gregory A Chass; Christopher J O'Brien; Niloufar Hadei; Eric Assen B Kantchev; Wei-Hua Mu; De-Cai Fang; Alan C Hopkinson; Imre G Csizmadia; Michael G Organ
Journal:  Chemistry       Date:  2009       Impact factor: 5.236

8.  Recent advances in efficient and selective synthesis of di-, tri-, and tetrasubstituted alkenes via Pd-catalyzed alkenylation-carbonyl olefination synergy.

Authors:  Ei-ichi Negishi; Zhihong Huang; Guangwei Wang; Swathi Mohan; Chao Wang; Hatsuhiko Hattori
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

9.  Palladium-catalyzed negishi cross-coupling reactions of unactivated alkyl iodides, bromides, chlorides, and tosylates.

Authors:  Jianrong Zhou; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2003-10-15       Impact factor: 15.419
  9 in total
  5 in total

1.  Highly selective reactions of unbiased alkenyl halides and alkylzinc halides: Negishi-Plus couplings.

Authors:  Arkady Krasovskiy; Bruce H Lipshutz
Journal:  Org Lett       Date:  2011-07-08       Impact factor: 6.005

2.  Suzuki-Miyaura cross-coupling of potassium dioxolanylethyltrifluoroborate and aryl/heteroaryl chlorides.

Authors:  Nicolas Fleury-Brégeot; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal:  Org Lett       Date:  2013-03-14       Impact factor: 6.005

3.  Catalysis in the Service of Green Chemistry: Nobel Prize-Winning Palladium-Catalysed Cross-Couplings, Run in Water at Room Temperature: Heck, Suzuki-Miyaura and Negishi reactions carried out in the absence of organic solvents, enabled by micellar catalysis.

Authors:  Bruce H Lipshutz; Benjamin R Taft; Alexander R Abela; Subir Ghorai; Arkady Krasovskiy; Christophe Duplais
Journal:  Platin Met Rev       Date:  2012-04

4.  Ni-catalyzed cross-electrophile coupling between vinyl/aryl and alkyl sulfonates: synthesis of cycloalkenes and modification of peptides.

Authors:  Jicheng Duan; Yun-Fei Du; Xiaobo Pang; Xing-Zhong Shu
Journal:  Chem Sci       Date:  2019-08-05       Impact factor: 9.825

Review 5.  Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm.

Authors:  Christopher S Horbaczewskyj; Ian J S Fairlamb
Journal:  Org Process Res Dev       Date:  2022-07-11       Impact factor: 3.858
  5 in total

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