Literature DB >> 18693766

One-pot Negishi cross-coupling reactions of in situ generated zinc reagents with aryl chlorides, bromides, and triflates.

Shohei Sase1, Milica Jaric, Albrecht Metzger, Vladimir Malakhov, Paul Knochel.   

Abstract

In situ generated aryl, heteroaryl, alkyl, or benzylic polyfunctional zinc reagents obtained by the addition of zinc and LiCl to the corresponding organic iodides undergo smooth Pd(0)-catalyzed cross-coupling reactions with aryl bromides, chlorides, and triflates in the presence of PEPPSI as a catalyst. This procedure avoids the manipulation of water and air-sensitive organozinc reagents and produces cross-coupling products in high yields.

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Year:  2008        PMID： 18693766     DOI： 10.1021/jo801063c

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


  14 in total

Review 1.  Nickel-catalyzed cross-couplings involving carbon-oxygen bonds.

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Review 2.  Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

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3.  Development of a new class of liver receptor homolog-1 (LRH-1) agonists by photoredox conjugate addition.

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4.  Reductive Decarboxylative Alkynylation of N-Hydroxyphthalimide Esters with Bromoalkynes.

Authors:  Liangbin Huang; Astrid M Olivares; Daniel J Weix
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-17       Impact factor: 15.336

5.  Site-Selective C-H alkylation of Complex Arenes by a Two-Step Aryl Thianthrenation-Reductive Alkylation Sequence.

Authors:  Beatrice Lansbergen; Paola Granatino; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2021-05-24       Impact factor: 15.419

6.  Replacing conventional carbon nucleophiles with electrophiles: nickel-catalyzed reductive alkylation of aryl bromides and chlorides.

Authors:  Daniel A Everson; Brittany A Jones; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2012-03-30       Impact factor: 15.419

7.  Methods and Mechanisms for Cross-Electrophile Coupling of Csp(2) Halides with Alkyl Electrophiles.

Authors:  Daniel J Weix
Journal:  Acc Chem Res       Date:  2015-05-26       Impact factor: 22.384

8.  Sequential Conia-ene-type cyclization and Negishi coupling by cooperative functions of B(C6F5)3, ZnI2, Pd(PPh3)4 and an amine.

Authors:  Min Cao; Ahmet Yesilcimen; Soumil Prasad; Jason Genova; Tanner Myers; Masayuki Wasa
Journal:  Org Biomol Chem       Date:  2020-09-23       Impact factor: 3.876

9.  A regioselectively 1,1',3,3'-tetrazincated ferrocene complex displaying core and peripheral reactivity.

Authors:  Gordon W Honeyman; David R Armstrong; William Clegg; Eva Hevia; Alan R Kennedy; Ross McLellan; Samantha A Orr; John A Parkinson; Donna L Ramsay; Stuart D Robertson; Stephen Towie; Robert E Mulvey
Journal:  Chem Sci       Date:  2020-03-27       Impact factor: 9.825

10.  Cross-electrophile coupling: principles of reactivity and selectivity.

Authors:  Daniel A Everson; Daniel J Weix
Journal:  J Org Chem       Date:  2014-05-15       Impact factor: 4.354
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