title: Organozinc Chemistry Enabled by Micellar Catalysis. Palladium-Catalyzed Cross-Couplings between Alkyl and ArylBromidesin Water at Room Temperature.
abstract: Negishi-like cross-couplings between (functionalized) alkyl and aryl bromides are described. Despite the fact that organozinc reagents are intolerant of water, their formation as well as their use in an aqueous micellar environment is discussed herein. Each component of this complex series of events leading up to C-C bond formation has an important role which has been determined insofar as the type of zinc, amine ligand, surfactant, and palladium catalyst are concerned. In particular, the nature of the surfactant has been found to be crucial in order to obtain synthetically useful results involving highly reactive, moisture-sensitive organometallics. Neither organic solvent nor heat is required for these cross-couplings to occur; just add water.
authors.affiliation: Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, United States.
authors.forename: Christophe
authors.initials: C
authors.lastname: Duplais
authors.forename: Arkady
authors.initials: A
authors.lastname: Krasovskiy
authors.forename: Bruce H
authors.initials: BH
authors.lastname: Lipshutz
references.citation: J Am Chem Soc. 2004 Feb 11;126(5):1340-1
references.pmid: 14759182
references.citation: J Am Chem Soc. 2009 Jul 22;131(28):9756-66
references.pmid: 19552426
references.citation: J Am Chem Soc. 2009 Jun 10;131(22):7532-3
references.pmid: 19441851
references.citation: J Org Chem. 2006 Feb 3;71(3):1104-10
references.pmid: 16438528
references.citation: Chem Asian J. 2011 Aug 1;6(8):1974-6
references.pmid: 21626709
references.citation: Chem Commun (Camb). 2011 May 28;47(20):5717-9
references.pmid: 21487612
references.citation: Acc Chem Res. 2008 Nov 18;41(11):1500-11
references.pmid: 18588321
references.citation: J Am Chem Soc. 2002 Nov 20;124(46):13856-63
references.pmid: 12431116
references.citation: J Org Chem. 2011 Jun 17;76(12):5061-73
references.pmid: 21539384
references.citation: J Am Chem Soc. 2008 Sep 24;130(38):12645-7
references.pmid: 18763769
references.citation: J Am Chem Soc. 2004 Jun 30;126(25):7788-9
references.pmid: 15212521
references.citation: J Am Chem Soc. 2008 Mar 19;130(11):3302-3
references.pmid: 18302392
references.citation: Org Lett. 2007 Aug 16;9(17):3253-4
references.pmid: 17655319
references.citation: Angew Chem Int Ed Engl. 2004 Jul 26;43(30):3955-7
references.pmid: 15274224
references.citation: Org Lett. 2007 Oct 25;9(22):4571-4
references.pmid: 17918950
references.citation: J Am Chem Soc. 2005 Apr 6;127(13):4594-5
references.pmid: 15796523
references.citation: Angew Chem Int Ed Engl. 2009;48(16):2969-72
references.pmid: 19288504
references.citation: Angew Chem Int Ed Engl. 2009;48(33):6045-8
references.pmid: 19593835
references.citation: Chem Commun (Camb). 2010 Jan 28;46(4):562-4
references.pmid: 20062862
references.citation: Org Lett. 2008 Aug 7;10(15):3259-62
references.pmid: 18611034
references.citation: Angew Chem Int Ed Engl. 2009;48(3):607-10
references.pmid: 19067450
references.citation: J Am Chem Soc. 2010 Aug 18;132(32):11027-9
references.pmid: 20698665
references.citation: Angew Chem Int Ed Engl. 2005 Jan 21;44(5):674-88
references.pmid: 15657966
references.citation: J Am Chem Soc. 2008 Jul 23;130(29):9257-9
references.pmid: 18582050
references.citation: J Am Chem Soc. 2010 Feb 3;132(4):1264-6
references.pmid: 20050651
references.citation: J Am Chem Soc. 2007 Aug 8;129(31):9602-3
references.pmid: 17628067
references.citation: J Am Chem Soc. 2006 Apr 26;128(16):5360-1
references.pmid: 16620105
references.citation: J Am Chem Soc. 2005 Aug 3;127(30):10482-3
references.pmid: 16045323
references.citation: Angew Chem Int Ed Engl. 2009;48(15):2656-70
references.pmid: 19173365
references.citation: J Am Chem Soc. 2005 Jan 19;127(2):510-1
references.pmid: 15643860
references.citation: J Am Chem Soc. 2004 Mar 31;126(12):3686-7
references.pmid: 15038701
references.citation: Chem Commun (Camb). 2005 Sep 7;(33):4161-3
references.pmid: 16100589
references.citation: Angew Chem Int Ed Engl. 2008;47(33):6278-82
references.pmid: 18613177
references.citation: J Am Chem Soc. 2008 May 28;130(21):6694-5
references.pmid: 18447357
references.citation: J Am Chem Soc. 2006 Jan 11;128(1):78-9
references.pmid: 16390130
references.citation: J Am Chem Soc. 2009 Nov 4;131(43):15592-3
references.pmid: 19827762
references.citation: J Am Chem Soc. 2010 Jan 27;132(3):920-1
references.pmid: 20047282
references.citation: Angew Chem Int Ed Engl. 2007;46(23):4364-6
references.pmid: 17465438
references.citation: J Org Chem. 2007 Jul 6;72(14):5104-12
references.pmid: 17550290
references.citation: Org Lett. 2006 Apr 27;8(9):1787-9
references.pmid: 16623551
references.citation: Angew Chem Int Ed Engl. 2006 Sep 11;45(36):6040-4
references.pmid: 16900548
references.citation: Org Lett. 2004 Apr 15;6(8):1297-9
references.pmid: 15070321
references.citation: Angew Chem Int Ed Engl. 2007;46(19):3556-8
references.pmid: 17444579
references.citation: Org Lett. 2010 Nov 5;12(21):4742-4
references.pmid: 20882969