Literature DB >> 35370453

Transition Metal Free sp3-sp3 carbon-carbon coupling between Benzylboronic Esters and Alkyl Bromides.

Richard W Russell1, Timothy J Barker1.   

Abstract

A transition metal free coupling reaction of benzylboronic esters and alkyl halides has been developed. Both alkyl bromides and alkyl iodides were found to be competent substrates with the nucleophilic boronate intermediate generated from the combination of benzylboronic ester and an alkyllithium. Good chemoselectivity was observed in substrates with a second electrophile. Both secondary and tertiary benzylboronic esters were effective nucleophiles in the reaction with primary alkyl halides. Mechanistic observations are consistent with a radical mechanism.

Entities:  

Year:  2021        PMID： 35370453      PMCID： PMC8966628          DOI： 10.1002/ejoc.202100361

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  25 in total

1.  PALLADIUM-CATALYZED ALKYL-ALKYL SUZUKI CROSS-COUPLINGS OF PRIMARY ALKYL BROMIDES AT ROOM-TEMPERATURE: (13-CHLOROTRIDECYLOXY)TRIETHYLSILANE [Silane, [(13-chlorotridecyl)oxy]triethyl-].

Authors:  Sha Lou; Gregory C Fu; Takuyo Higo; Tohru Fukuyama
Journal:  Organic Synth       Date:  2010-01-01

2.  Method for palladium-catalyzed cross-couplings of simple alkyl chlorides: Suzuki reactions catalyzed by [Pd2(dba)3]/PCy3.

Authors:  Jan H Kirchhoff; Chaoyang Dai; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2002-06-03       Impact factor: 15.336

3.  Stereoconvergent amine-directed alkyl-alkyl Suzuki reactions of unactivated secondary alkyl chlorides.

Authors:  Zhe Lu; Ashraf Wilsily; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2011-05-10       Impact factor: 15.419

4.  Beyond benzyl grignards: facile generation of benzyl carbanions from styrenes.

Authors:  R David Grigg; Jared W Rigoli; Ryan Van Hoveln; Samuel Neale; Jennifer M Schomaker
Journal:  Chemistry       Date:  2012-06-20       Impact factor: 5.236

5.  Asymmetric alkyl-alkyl cross-couplings of unactivated secondary alkyl electrophiles: stereoconvergent Suzuki reactions of racemic acylated halohydrins.

Authors:  Nathan A Owston; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2010-09-01       Impact factor: 15.419

6.  Asymmetric Suzuki cross-couplings of activated secondary alkyl electrophiles: arylations of racemic alpha-chloroamides.

Authors:  Pamela M Lundin; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

7.  Benzylation of Imines with Activated Boronate Nucleophiles.

Authors:  Michael R Hollerbach; Jacob C Hayes; Timothy J Barker
Journal:  European J Org Chem       Date:  2019-01-21

8.  Enantioselective alkyl-alkyl Suzuki cross-couplings of unactivated homobenzylic halides.

Authors:  Bunnai Saito; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2008-05-01       Impact factor: 15.419

9.  Alkyl-alkyl suzuki cross-couplings of unactivated secondary alkyl halides at room temperature.

Authors:  Bunnai Saito; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2007-07-12       Impact factor: 15.419

Review 10.  Transition-Metal Catalysis of Nucleophilic Substitution Reactions: A Radical Alternative to SN1 and SN2 Processes.

Authors:  Gregory C Fu
Journal:  ACS Cent Sci       Date:  2017-06-12       Impact factor: 14.553
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  1 in total

1.  Merging Halogen-Atom Transfer (XAT) and Copper Catalysis for the Modular Suzuki-Miyaura-Type Cross-Coupling of Alkyl Iodides and Organoborons.

Authors:  Zhenhua Zhang; Bartosz Górski; Daniele Leonori
Journal:  J Am Chem Soc       Date:  2022-01-21       Impact factor: 16.383
  1 in total

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