SNIECKUS GROUP RESEARCH PAGES

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2013

       
           
                    ==> A Practical in situ Generation of the Schwartz Reagent. Reduction of Tertiary Amides to Aldehydes and Hydrozirconation  
  Zhao, Y., Snieckus, V. Org. Lett. 2013,  Article ASAP, DOI: 10.1021/ol403183a  
 

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                   ==> Reductive Cleavage of Aryl O-Carbamates to Phenols by the Schwartz Reagent. Expedient Link to the Directed Ortho Metalation Strategy  
  Zhao, Y., Morin, J., Snieckus, V. Org. Lett. 2013, 15,  4102–4105  
 

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                   ==> The Directed ortho Metalation–Cross Coupling Fusion. Development and Application in Synthesis  
  Board, J., Cosman, J., Singh, S., Rantanen, T., Snieckus, V., Platinum Metals Rev., 2013, 57, 234–258  
     
 
 

2012

       
           
                   ==> Palladium-Catalyzed Cross-Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize  
  Johansson Seechurn, C.C.C., Kitching, M.O., Colacot, T.J., Snieckus, V., Angew. Chem. Int. Ed. 2012, 51, 5062-5085  
     
                   ==> Organic chemistry: Directors extend their reach  
  Kitching, M.O.,  Snieckus, V., Nature 2012, 486, 478-479  
     
                   ==> Toxicity of Hydroxylated Alkyl-Phenanthrenes to the Early Life Stages of Japanese Medaka (Oryzias latipes)  
  Fallahtafti, S.,  Rantanen, T., Brown, R.S., Snieckus, V., Hodson, P.V.,  Aquatic Toxicology,  2012, 106-107, 56-64  
     
                   ==> Copper-Catalyzed Cross-Coupling Interrupted by an Opportunistic Smiles Rearrangement: An Efficient Domino Approach to Dibenzoxazepinones  
  Kitching, M.O., Hurst, T.E.,  Snieckus, V. Angew. Chem. Int. Ed., 2012, 51, 2925–2929  
 

http://onlinelibrary.wiley.com/store/10.1002/anie.201106786/asset/image_m/mcontent.gif?v=1&s=ded8a697316f96ae381611832a0a8f4449988aff

 
     
                   ==> In Situ Anionic Shielding for Regioselective Metalation: Directed peri and Iterative Metalation Routes to Polyfunctionalized 7-Azaindoles  
  Schneider, C., David, E., Toutov, A., Snieckus, V., Angew. Chem. Int. Ed., 2012, 51, 2722 – 2726  
 

 
     
                   ==> Endo functionalization of Tröger's Base via Reactions of its Twisted Amide Analogues  
  Artacho, J., Ascic, E.,  Rantanen, T.,  Wallentin, C.,  Harmata, M., Snieckus, V., Wärnmark, K., Org. Lett., 2012, 14, 4706-4709  
 

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                   ==>  
  Artacho, J., Ascic, E., Rantanen, T.,  Karlsson, J., Wallentin, C.-J., Wang, R., Wendt, O. F., Harmata, M., Snieckus, V., Wärnmark, K., Chem. Eur. J. 2012, 18, 1038-1042  
     
     
                   ==> Dizincation of a 2-Substituted Thiophene: Constructing a Cage with a [16]Crown-4 Zincocyclic Core  
  Balloch, L.,  Garden, J.,  Kennedy, A.R., Mulvey, R.E., Rantanen, T.,  Robertson, S.D.,  Snieckus, V., Angew. Chem. Int. Ed. 2012, 51, 6934-6937  
     
                   ==> Directed Metalation-Cross-Coupling Strategies. Total Syntheses of the Alleged and the Revised Phenanthrene Natural Product Gymnopusin  
  Fu, J.,  Wang, X.,  Snieckus, V.,  Helv. Chim. Acta, 2012, 95, 2680-2694  
     
                   ==> Combined Directed Metalation – Suzuki-Miyaura Cross Coupling Strategies. Synthesis of Isomeric Chromenopyridinones and Related Annulated Analogues  
  Miller, R.E., Summer, R., Fan, H.,  Snieckus, V.,  Groth, U., Heterocycles, 2012, 86, 1045-1054  
     
2011
                   ==> Concerning the Structures of Alkali-Metal-Mediated ortho Zincation of Benzamides and Phenyl O-Carbamate  
  Rantanen, T., Balloch, L., Kennedy, A., Mulvey, E., Robertson, S., Snieckus, V., Organometallics, 2011, 30, 145-152  
     
                   ==> Suzuki-Miyaura Cross-Coupling of Aryl Carbamates and Sulfamates: Experimental and Computational Studies  
  Quasdorf, KW,  Antoft-Finch, A., Liu, P., Silberstein, A.L.,  (Komaromi, A.,  Blackburn, T., Ramgren, S.D., Houk, K. N., Snieckus, V., Garg, N.K.,  J. Am. Chem. Soc., 2011, 133, 6352-6363.  
 

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                   ==> Directed aromatic functionalization  
  Snieckus, V., Beilstein J. Org. Chem. 2011, 7, 1215-1218  
     
                   ==> Directed ortho-Metalation-Cross-Coupling Strategies. One-Pot Suzuki Reaction to Biaryl and Heterobiaryl Sulfonamides  
  Schneider, C., Broda, E., Snieckus, V. Org. Lett., 2011, 13, 3588-3591  
 

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2010

     
                   ==> 'COMBINED DIRECTED ORTHO METALATION-HALOGEN DANCE (HD) SYNTHETIC STRATEGIES FOR POLYSUBSTITUTED AROMATICS AND PYRIDINES.
HD-ANIONIC ORTHO FRIES REARRANGEMENT AND DOUBLE HD SEQUENCES'
RE MILLER, T RANTANEN, KA OGILVIE, U GROTH AND V SNIECKUS, ORG. LETT., 2010, 12, 2198-2201
 

 
                   ==> 'IRIDIUM-CATALYZED C-H ACTIVATION VERSUS DIRECTED ORTHO METALATION: COMPLEMENTARY BORYLATION OF AROMATICS AND
HETEROAROMATICS'
TE HURST, TK MACKLIN, M BECKER, E HARTMANN, W KUGEL, J-C PARISIENNE-LA SALLE,
AS BATSANOV, TB MARDER AND V SNIECKUS, CHEM. EUR. J., 2010, 16, 8155-8161
 

 
                   ==> 'ON THE MECHANISM OF THE DIRECTED ORTHO AND REMOTE METALATION REACTIONS OF N,N-DIALKYLBIPHENYL 2-CARBOXAMIDES'
D TILLY, J-M FU, B-P ZHAO, M ALESSI, A-S CASTANET, V SNIECKUS AND J MORTIER, ORG. LETT., 2010, 12, 68-71
 

 
2009
                   ==> 'N,N-DIETHYL O-CARBAMATE: DIRECTED METALATION GROUP AND ORTHOGONAL SUZUKI-MIYAURA CROSS COUPLING PARTNER'
A ANTOFT-FINCH, T BLACKBURN AND V SNIECKUS, J. AM. CHEM. SOC., 2009, 131, 17750-17752
 

 
                   ==> 'SYNTHESIS OF SUBSTITUTED IMIDAZO[1,5-A]PYRAZINES VIA MONO-, DI-, AND DIRECTED REMOTE METALATION STRATEGIES'
J BOARD, J-X WANG, AP CREW, MZ JIN, K FOREMAN, MJ MULVIHILL AND V SNIECKUS, ORG. LETT., 2009, 11, 5118-5121
 

 
                   ==> 'COMBINED DIRECTED ORTHO AND REMOTE METALATION-SUZUKI CROSS COUPLING STRATEGIES. EFFICIENT SYNTHESIS OF HETEROARYL-FUSED
BENZOPYRANONES FROM BIARYL O-CARBAMATES'
CA JAMES, AL COELHO, M GEVAERT, P FORGIONE AND V SNIECKUS, J. ORG. CHEM., 2009, 74, 4094-4103
 

 
                   ==> 'COMBINED DIRECTED ORTHO AND REMOTE METALATION-SUZUKI CROSS COUPLING STRATEGIES. THE TOTAL SYNTHESIS OF THE AGLYCONES
OF THE GILVOCARCINS V, M, AND E AND ARNOTTIN I'
CA JAMES AND V SNIECKUS, J. ORG. CHEM., 2009, 74, 4080-4093
 

 
                   ==> 'GAMMA-SILYLATED ALPHA,BETA-UNSATURATED AMIDES - PREPARATION BY [1,5]SIGMATROPIC REARRANGEMENT AND USE AS MASKED
DIENOLATE EQUIVALENTS IN CARBONYL CONDENSATIONS'
JR GREEN, BI ALO, M MAJEWSKI AND V SNIECKUS, CAN. J. CHEM., 2009, 87, 745-759
     
                   ==> 'STUDIES OF A RING-CLEAVING DIOXYGENASE ILLUMINATE THE ROLE OF CHOLESTEROL METABOLISM IN THE PATHOGENESIS OF
MYCOBACTERIUM TUBERCULOSIS'
KC YAM, I D'ANGELO, R KALSCHEUER, H ZHU, J-X WANG, V SNIECKUS, LH LY, PJ CONVERSE,
WR JACOBS, JR., N STRYNADKA AND LINDSAY ELTIS, PLOS PATHOGENS, 2009, 5, E1000344
                   ==> 'NATURE'S CHEMISTRY'
V SNIECKUS, CHEM AND ENG NEWS, 2009, 87, 4
2008
                   ==> 'CARBANIONIC FRIEDEL-CRAFTS EQUIVALENTS. REGIOSELECTIVE DIRECTED ORTHO AND REMOTE METALATION/C-N CROSS COUPLING
ROUTES TO ACRIDONES AND DIBENZO[B,F]AZEPINONES'
SL MACNEIL, M GRAY, DG GUSEV, LE BRIGGS AND V SNIECKUS, J. ORG. CHEM., 2008, 73, 9710-9719
 

 
                   ==> 'PALLADIUM-CATALYZED DIRECT HECK ARYLATION OF DUAL PI-DEFICIENT/PI-EXCESSIVE HETEROAROMATICS.
SYNTHESIS OF C-5 ARYLATED IMIDAZO[1,5-A]PYRAZINES'
J-X WANG, JA MCCUBBIN, M JIN, R LAUFER, Y MAO, AP CREW, MJ MULVIHILL AND V SNIECKUS, ORG. LETT., 2008, 10, 2923-2926
 

 
                   ==> 'ANIONIC INDOLE N-CARBAMOYL N TO C TRANSLOCATION. A DIRECTED REMOTE METALATION ROUTE TO 2-ARYL- AND 2-HETEROARYLINDOLES.
SYNTHESIS OF BENZ[A]CARBAZOLES AND INDENO[1,2-B]INDOLES'
Z ZHAO, A JAWORSKI, I PIEL AND V SNIECKUS, ORG. LETT., 2008, 10, 2617-2620
 

 
                   ==> 'COMBINED METALATION-CROSS COUPLING STRATEGIES: A SYNTHESIS OF SCHUMANNIOPHYTINE BY A KEY BIARYL O-CARBAMATE REMOTE
ANIONIC FRIES REARRANGEMENT'
TK MACKLIN, MA REED AND V SNIECKUS, EUR. J. ORG. CHEM., 2008, 9, 1507-1509
 

 
                   ==> 'CARBAMOYL TRANSLOCATIONS BY AN ANIONIC ORTHO-FRIES CUMULENOLATE ALPHA-ACYLATION PATHWAY:
REGIOSELECTIVE SYNTHESIS OF POLYSUBSTITUTED CHROMENE 3- AND 8-CARBOXAMIDES'
TK MACKLIN, J PANTELEEV AND V SNIECKUS, ANGEW. CHEM. INT. ED., 2008, 47, 2097-2101
 

 
 
                   ==> 'ALBERT I MEYERS (1933-2007) - OBITUARY'
V SNIECKUS, ANGEW. CHEM. INT. ED., 2008, 47, 1986-1987
 
2007
 
 
                   ==> '3,3'-DIPYRIDYL BINOL LIGANDS. SYNTHESIS AND APPLICATION IN ENANTIOSELECTIVE ADDITION OF ET2ZN TO ALDEHYDES'
RR MILBURN, SMS HUSSAIN, O PRIEN, Z AHMED AND V SNIECKUS, ORG. LETT., 2007, 9, 4403-4406
 

 
 
                   ==> 'COMBINED DIRECTED ORTHO METALATION / SUZUKI-MIYAURA CROSS-COUPLING STRATEGIES. REGIOSPECIFIC SYNTHESIS OF
CHLORODIHYDROXYBIPHENYLS AND POLYCHLORINATED BIPHENYLS'

S NERDINGER, C KENDALL, X CAI, R MARCHART, P RIEBEL, MR JOHNSON, CF YIN, N HENAFF, LD ELTIS AND V SNIECKUS,

J. ORG. CHEM., 2007, 72, 5960-5967
 

 
 
                   ==>

'DIRECTED ORTHO METALATION / CROSS-COUPLING STRATEGIES. N-CUMYL ARYLSULFONATES. FACILE DEPROTECTION AND

EXPEDIENTROUTE TO 7- AND 4,7-SUBSTITUTED SACCHARARINS'

J BLANCHET, TK MACKLIN, P ANG, C METALLINOS AND V SNIECKUS, J. ORG. CHEM., 2007, 72, 3199-3206

 

 
 
                   ==>

'DIRECTED ORTHO METALATION-BORONATION AND SUZUKI-MIYAURA CROSS-COUPLING OF PYRIDINE DERIVATIVES:

A ONE-POT PROTOCOL TO SUBSTITUTED AZABIARYLS'

M ALESSI, AL LARKIN, KA OGILVIE, LA GREEN, S LAI, S LOPEZ AND V SNIECKUS, J. ORG. CHEM., 2007, 72, 1588-1594

 

 
 
                   ==> 'ENTHRALLING ODOURS'
V SNIECKUS, CHEM AND ENG NEWS, 2007, 85, 3
 
2006
 
                   ==> 'A MIXED NAPHTHYL-PHENYL PHOSPHINE LIGAND MOTIF FOR SUZUKI, HECK, AND HYDRODEHALOGENATION REACTIONS'
OM DEMCHUK, B YORUK, T BLACKBURN AND V SNIECKUS, SYNLETT, 2006, 18, 2908-2913
 
                   ==> 'LAUDATION FOR PROFESSOR RICHARD HECK'
D TABER AND V SNIECKUS, SYNLETT, 2006, 18, III-IV
 
                   ==> 'DEPROTONATION OF BETA,BETA-DISUBSTITUTED ALPHA,BETA-UNSATURATED AMIDES - MECHANISM AND STEREOCHEMICAL CONSEQUENCES'
JR GREEN, M MAJEWSKI AND V SNIECKUS, CAN. J. CHEM., 2006, 84, 1397-1410
 
                   ==> 'ASYMMETRIC TOTAL SYNTHESIS OF (-)-PANACENE AND CORRECTION OF ITS RELATIVE CONFIGURATION'
J BOUKOUVALAS, M POULIOT, J ROBICHAUD, SL MACNEIL AND V SNIECKUS, ORG. LETT., 2006, 8, 3597-3599
 

 
 
                   ==> 'ANIONIC N-FRIES REARRANGEMENT OF N-CARBAMOYL DIARYLAMINES TO ANTHRANILAMIDES. METHODOLOGY AND APPLICATION
TO ACRIDONE AND PYRANOACRIDONE ALKALOIDS'
SL MACNEIL, BJ WILSON AND V SNIECKUS, ORG. LETT., 2006, 8, 1133-1136
 

 
                   ==> '(-)-SPARTEINE-MEDIATED STEREOSELECTIVE DIRECT ORTHO METALATION OF FERROCENE DIAMIDES'
R LAUFER, U VEITH, NJ TAYLOR AND V SNIECKUS, CAN. J. CHEM., 2006, 84, 356-369