Chem 634 February 10 2004 References Week 1 corresponding authors in bold font Prof Fox 1 Activation of Grignard Reagents Lai Y H Synthesis 1981 585 2 Li R SPh R Li Screttas C G Micha Screttas M Hydrolithiation of alpha olefins by a regiospecific two step process Transformation of alkyl phenyl sulfides to alkyllithium reagents J Org Chem 1978 43 1064 1071 3 I Mg iPr iPr2Mg Rottlander M B L Cahiez G Knochel P Stereoselective Preparation of Functionalized Alkenylmagnesium Reagents via an Iodine Magnesium Exchange Reaction J Org Chem 1999 1999 1080 1081 4 ArI iPrMgBr ArMgBr Boymond L Rottl nder M Cahiez G Knochel P Preparation of Highly Functionalized Grignard Reagents by an Iodine Magnesium Exchange Reaction and its Application in Solid Phase Synthesis Angew Chem Int Ed 1998 37 1701 1703 5 Directed Metallation Snieckus V Directed ortho metalation Tertiary amide and O carbamate directors in synthetic strategies for polysubstituted aromatica Chem Rev 1990 90 879 6 Ph2CuLi x ray structure Nis Peter Lorenzen Erwin Weiss Synthesis and Structure of a Dimeric Lithium Diphenylcuprate Li OEt 2 CuPh2 2 Angew Chem Int Ed 1990 29 300 7 Synthesis of Cuprate reagents that bear functional groups RZnI CuCN LiX R CuCN ZnI Knochel P Yeh M C P Berk S C Talbert J Synthesis and reactivity toward acyl chlorides and enones of the new highly functionalized copper reagents RCu CN ZnI J Org Chem 1988 53 2390 2392 General References to Cuprate Chemistry 8 Lipshutz B H Sengupta S Organocopper reagents Substitution conjugate addition carbo metallocupration and other reactions Org React N Y 1992 41 136 9 Lipshutz B H The Evolution of Higher Order Cyanocuprates Synlett 1990 119 10 Lipshutz B H Wilhelm R S Chemistry of higher order mixed organocuprates The stereochemical outcome of substitution reactions at unactivated secondary centers using organocopper reagents J Am Chem Soc 1982 104 46964698 Et2 CuLi I Et or Et2Cu CN Li2 racemic Et Me CuLi Br Et or Et2Cu CN Li2 100 inversion 11 Chelation controlled SN2 Ph Ph Me2 CuLi D O PhN Me D O Gallina C Ciattini P G Conversion of allylic carbamates into olefins with lithium dimethylcuprate A new formal SN2 reaction J Am Chem Soc 1979 101 1035 1036 Goering H L Kantner S S Tseng C C Alkylation of allylic derivatives 4 On the mechanism of alkylation of allylic N phenylcarbamates with lithium dialkylcuprates J Org Chem 1983 48 715 721 12 SN2 w o chelate CH3 CH3 H3 C D O BuMgBr 10 CuCN O H3 C Bu D CH3 Tseng C C Paisley S D Goering H L Alkylation of allylic derivatives 11 Copper I catalyzed cross coupling of allylic carboxylates with Grignard reagents J Org Chem 1986 51 2884 2891 13 For a discussion of the diaxial opening of cyclohexene oxide see pp 526 531 of Eliel and Wilen Stereochemistry of Organic Compounds 14 1 4 addition of cyanocuprates to allylic epoxides Marino J P Jaen J C Stereospecific umpolung alpha substitution of ketones via reactions of organocuprates with enol ethers of alpha beta epoxycyclohexanones J Am Chem Soc 1982 104 3165 3172 Marino J P Floyd D M Tetrahedron Lett 1979 675 Wender P A Erhardt J M Letendre L J Reaction of allylically substituted enolates with organometallic reagents a convenient source of enolonium ion equivalents J Am Chem Soc 1981 103 2114 2116 15 Pd catalyzed Cross coupling Reactions Couplings of Aryl Chlorides Littke A F Fu G C Palladium catalyzed coupling reactions of aryl chlorides Angew Chem Int Ed Engl 2002 41 4176 4211 Heck Reaction Whitcombe N J Hii K K Gibson S E Advances in the Heck chemistry of aryl bromides and chlorides Tetrahedron 2001 57 7449 7476 Heck R F Palladium Catalysed Vinylation of Organic Halides Org React N Y 1982 27 345 Suzuki Suzuki A Cross coupling reactions via organoboranes J Organomet Chem 2002 653 83 90 Kotha S Lahiri K Kashinath D Recent applications of the Suzuki Miyaura crosscoupling reaction in organic synthesis Tetrahedron 2002 58 9633 9695 Suzuki A Brown H C Organic Synthesis via Boranes Vol 3 Aldrich Milwaukee WI 2003 Stille Farina V Krishnamurthy V Scott W J The Stille Reaction Org React N Y 1997 50 1 652 Kosugi M Fugami K Overview of the Stille Protocol with Sn In Handbook of Organopalladium Chemistry for Organic Synthesis Negishi E i de Meijere A Eds Wiley Interscience 2002 Vol 1 pp 263 285 Sonogashira Reaction Sonogashira K Development of Pd Cu catalyzed cross coupling of terminal acetylenes with sp2 carbon halides J Organomet Chem 2002 653 46 49 Sonogashira K Cross coupling reactions to sp carbon atoms In Metal Catalyzed Cross Coupling Reactions Diederich F Stang P J Eds Wiley VCH Inc 605 Third Ave New York NY 10158 0012 1998 pp 203 229 Axel K llhofer T P Herbert Plenio A Versatile Catalyst for the Sonogashira Coupling of Aryl Chlorides Angew Chem Int Ed 2003 42 1056 1058 Amination and C O bond formation Muci A R Buchwald S L Cross Coupling Reactions Practical palladium catalysts for C N and C O bond formation Top Curr Chem 2002 219 131 209 Hartwig J F Palladium catalyzed amination of aryl halides and related reactions In Handbook of Organopalladium Chemistry for Organic Synthesis Negishi E i de Meijere A Eds Wiley Interscience 2002 Vol 1 pp 1051 1096 Ketone arylation Fox J M Huang X Chieffi A Buchwald S L Highly Active and Selective Catalysts for the Formation of Aryl Ketones J Am Chem Soc 2000 122 7 13601370 16 R1ZnX R2COCl cat Pd 0 R1COR2 Negishi E i et al Palladium Catalyzed Acylation of Organozincs and other Organometallics as a Convenient Route to Ketone Tetrahedron Lett 1983 24 5181 17 R Br R BBN Pd OAc 2 PCy 3 R R Netherton M R Dai C Neuschutz K Fu G C Room Temperature Alkyl Alkyl Suzuki Cross Coupling of Alkyl Bromides that Possess Hydrogens J Am Chem Soc 2001 123 10099 10100 18 Review of Collman s Reagent Na2Fe CO 4 Collman J P Disodium Tetracarbonylferrate a Transition Metal Analog of a Grignard Reagent Acc Chem Res 1975 8 342 19 Cyanation of Arylhalides and aryldiazonium salts Review Lindley J A Copper Assisted Nucleophilic Substitution of Aryl Halogen Tetrahedron 1984 40 1433 Mark Sundermeier A Z Matthias Beller Palladium Catalyzed Cyanation of Aryl Halides Recent Developments and Perspectives European Journal of Inorganic Chemistry 2003 19 3513 3526 Jin F Confalone P N Palladium catalyzed cyanation reactions of aryl chlorides Tetrahedron Lett 2000 41 3271 3273 S L Buchwald Copper Catalyzed Domino Halide Exhange Cyanation of Aryl Bromides J Am Chem Soc 2003 125 2890 20 Weinreb s Amide O R OMe N Me O R MgX or R Li R R Nahm and Weinreb Tetrahedron Lett 1981 22 3815 Review Sibi M P