Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 20
365
Views
12
CrossRef citations to date
0
Altmetric
Original Articles

Tandem Pd/C‐Catalyzed Reductive Coupling and Dehalogenation of Benzylic Halides

, , , &
Pages 2715-2722 | Received 28 Apr 2005, Published online: 22 Aug 2006

References

  • Amatore , C. and Jutand , A. 2000 . Anionic Pd (0) and Pd (II) intermediates in palladium‐catalyzed Heck and cross‐coupling reactions . Acc. Chem. Res. , 33 ( 5 ) : 314 – 321 .
  • Hassan , J. , Sevignon , M. , Gozzi , C. , Schulz , E. and Lemaire , M. 2002 . Aryl‐aryl bond formation one century after the discovery of the Ullmann reaction . Chem. Rev. , 102 ( 5 ) : 1359 – 1469 .
  • Littke , A. F. and Fu , G. C. 2002 . Palladium‐catalyzed coupling reactions of aryl chlorides . Angew. Chem., Int. Ed. Engl. , 41 ( 22 ) : 4176 – 4211 .
  • Inaba , S. , Matsumoto , H. and Rieke , R. D. 1984 . Highly reactive metallic nickel—reductive homocoupling reagent for benzylic monohalides and polyhalides . J. Org. Chem. , 49 ( 12 ) : 2093 – 2098 .
  • Ashby , E. C. and Alfekri , D. M. 1990 . The reaction of benzotrihalides and benzal halides with magnesium—synthetic and mechanistic studies . J. Organometal. Chem. , 390 ( 3 ) : 275 – 292 .
  • Ranu , B. C. , Dutta , P. and Sarkar , A. 1998 . Indium‐promoted reductive homocoupling of alkyl and aryl halides . Tetrahedron Lett. , 39 ( 51 ) : 9557 – 9558 .
  • Ogata , Y. and Nakamura , H. 1956 . A note on the dechlorination condensation of benzal chloride and benzotrichloride by iron and water . J. Org. Chem. , 21 ( 10 ) : 1170 – 1171 .
  • Ma , J. and Chan , T.‐H. 1998 . Organometallic‐type reactions in aqueous media. Wurtz‐coupling of alkyl halides with manganese/cupric chloride . Tetrahedron Lett. , 39 ( 17 ) : 2499 – 2502 .
  • de Sa , A. C. P. F. , Pontes , G. M. A. , dos Anjos , J. A. L. , Santana , S. R. , Bieber , L. W. and Malvestiti , I. 2003 . Reductive coupling reaction of benzyl, allyl and alkyl halides in aqueous medium promoted by zinc . J. Braz. Chem. Soc. , 14 ( 3 ) : 429 – 434 .
  • Hashimoto , I. , Tsuruta , N. , Ryang , M. and Tsutsumi , S. 1970 . The reaction of potassium hexacyanodinickelate(1) with organic halides . J. Org. Chem. , 35 ( 11 ) : 3748 – 3752 .
  • Yamada , Y. and Momose , D. 1981 . Reductive coupling of benzylic halides by chlorotris(triphenylphosphine)cobalt(I) . Chem. Lett. , : 1277 – 1278 .
  • Cooper , T. A. 1973 . Reductive coupling of aralkyl halides by vanadium(II) . J. Am. Chem. Soc. , 95 ( 13 ) : 4158 – 4162 .
  • Yoshisato , E. and Tsutsumi , S. 1968 . Reactions of benzyl halides with nickel carbonyl in various media . J. Org. Chem. , 33 ( 2 ) : 869 – 871 .
  • Seyferth , D. and Millar , M. D. 1972 . Reactions of dicobalt octacarbonyl and related compounds with gem‐dihalides . J. Organomet. Chem. , 38 ( 2 ) : 373 – 383 .
  • Coffey , C. E. 1961 . Reaction of iron pentacarbonyl with gem‐dihalides . J. Am. Chem. Soc. , 83 ( 7 ) : 1623 – 1626 .
  • Alper , H. and Des Roches , D. 1976 . Dehalogenation and condensation reactions of molybdenum carbonyls with activated halides . J. Org. Chem. , 41 ( 5 ) : 806 – 808 .
  • Pinault , F. S. and Crumbliss , A. L. 1981 . Cobaloxime(II)‐initiated coupling of alpha, alpha,alpha‐trihalomethylbenzenes . J. Organomet. Chem. , 215 ( 2 ) : 229 – 239 .
  • Geering , E. J. Oct. 11 1966 . “ Benzothiophenes ” . Oct. 11 , US patent 3,278,552
  • Kaufman , S. A. , Phanijphand , T. and Fry , A. J. 1996 . Cobalt (salen)‐electrocatalyzed conversion of benzotrichloride into tolane. A triply catalytic and overall quintuple electrochemical transformation . Tetrahedron Lett. , 37 ( 45 ) : 8105 – 8108 .
  • Fry , A. J. and Singh , A. H. 1994 . Cobalt (salen)‐electrocatalyzed reduction of benzal chloride—dependence of products upon electrolysis potential . J. Org. Chem. , 59 ( 26 ) : 8172 – 8177 .
  • Nedelec , J. Y. , Perichon , J. and Troupel , M. 1997 . Organic electroreductive coupling reactions using transition metal complexes as catalysts . Top. Curr. Chem. , 185 : 141 – 173 . and reference cited therein
  • Mukhopadhyay , S. , Rothenberg , G. , Gitis , D. and Sasson , Y. 2000 . Tandem one‐pot palladium‐catalyzed reductive and oxidative coupling of benzene and chlorobenzene . J. Org. Chem. , 65 ( 10 ) : 3107 – 3110 .
  • Mukhopadhyay , S. , Rothenberg , G. , Wiener , H. and Sasson , Y. 1999 . Palladium‐catalyzed aryl‐aryl coupling in water using molecular hydrogen: Kinetics and process optimization of a solid‐liquid‐gas system . Tetrahedron , 55 ( 51 ) : 14763 – 14768 .
  • Mukhopadhyay , S. , Rothenberg , G. , Gitis , D. and Sasson , Y. 2000 . On the mechanism of palladium‐catalyzed coupling of haloaryls to biaryls in water with zinc . Org. Lett. , 2 ( 2 ) : 211 – 214 .
  • Mukhopadhyay , S. , Rothenberg , G. , Joshi , A. , Baidossi , M. and Sasson , Y. 2002 . Heterogeneous palladium‐catalysed heck reaction of aryl chlorides and styrene in water under mild conditions . Adv. Synth. Catal. , 344 ( 3–4 ) : 348 – 354 .
  • Wiener , H. , Blum , J. and Sasson , Y. 1991 . Studies on the mechanism of transfer hydrogenation of nitroarenes by formate salts catalyzed by Pd/C . J. Org. Chem. , 56 ( 14 ) : 4481 – 4486 .
  • Mukhopadhyay , S. , Rothenberg , G. , Gitis , D. , Wiener , H. and Sasson , Y. 1999 . Kinetics and mechanism of heterogeneous palladium‐catalyzed coupling reactions of chloroaryls in water . J. Chem. Soc., Perkin Trans. 2 , 2 ( 9 ) : 2481 – 2484 .
  • Wiener , H. , Sasson , Y. and Blum , J. 1986 . Palladium‐catalyzed decomposition of aqueous alkali‐metal formate solutions . J. Mol. Catal. , 35 ( 3 ) : 277 – 284 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.