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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2010 - Issue 1
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Original Articles

Pd–NHC Catalyzed Biaryl Coupling by Direct C–H Activation—A Novel Strategy for the Synthesis of Dibenzocyclooctane Lignans

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Pages 41-51 | Received 08 Sep 2009, Published online: 14 Dec 2010

REFERENCES

  • Marion , N. ; Navarro , O. ; Mei , J. ; Stevens , E. D. ; Scott , N. M. ; Nolan , S. P. Modified (NHC)Pd(allyl)Cl (NHC = N-Heterocyclic Carbene) complexes for room-temperature Suzuki–Miyaura and Buchwald–Hartwig reactions . J. Am. Chem. Soc. 2006 , 128 , 4101 – 4111 .
  • (a) Guram , A. S. ; Rennels , R. A. ; Buchwald , S. L. A simple catalytic method for the conversion of aryl bromides to arylamines . Angew. Chem., Int. Ed. Engl. 1995 , 34 , 1348 – 1350 ; (b) Louie , J. ; Hartwig , J. F. Palladium-catalyzed synthesis of arylamines from aryl halides. Mechanistic studies lead to coupling in the absence of tin reagents . Tetrahedron Lett. 1995 , 36 , 3609 – 3612 ; (c) Muci , A. R. ; Buchwald , S. L. Practical palladium catalysts for C–N and C–O bond formation . Top. Curr. Chem. 2002 , 219 , 131 – 209 .
  • (a) Antilla , J. C. ; Buchwald , S. L. Copper-catalyzed coupling of arylboronic acids and amines . Org. Lett. 2001 , 3 , 2077 – 2079 ; (b) Kwong , F. Y. ; Buchwald , S. L. Mild and efficient copper-catalyzed amination of aryl bromides with primary alkylamines . Org. Lett. 2003 , 5 , 793 – 796 ; (c) Omar-Amrani , R. ; Thomas , A. ; Brenner , E. ; Schneider , R. ; Fort , Y. Efficient nickel-mediated intramolecular amination of aryl chlorides . Org. Lett. 2003 , 5 , 2311 – 2313 ; (d) Desmarets , C. ; Schneider , R. ; Fort , Y. Nickel(0)/dihydroimidazol-2-ylidene complex catalyzed coupling of aryl chlorides and amines . J. Org. Chem. 2002 , 67 , 3029 – 3036 .
  • Lloyd-Williams , P. ; Giralt , E. Atropisomerism, biphenyls and the Suzuki coupling: Peptide antibiotics. Chem. Soc. Rev. 2001, 30, 145–157.
  • Pu , L. 1,1′-binaphthyl dimers, oligomers, and polymers: Molecular recognition, asymmetric catalysis, and new materials . Chem. Rev. 1998 , 98 , 2405 – 2494 .
  • Bourissou , D. ; Guerret , O. ; Gabbai , F. P. ; Bertrand , G. Stable carbenes . Chem. Rev. 2000 , 100 , 39 – 92 .
  • Campeau , L. C. ; Thansandote , P. ; Fagnou , K. High-yielding intramolecular direct arylation reactions with aryl chlorides . Org. Lett. 2007 , 7 , 1857 – 1860 .
  • Organ , M. G. ; Abdel-Hadi , M. ; Avola , S. ; Dubovyk , I. ; Hadei , N. ; Kantchev , E. A. B. ; O'Brien , C. J. ; Sayah , M. ; Valente , C. Pd-catalyzed aryl amination mediated by well defined, N-heterocyclic carbene (NHC)–Pd precatalysts, PEPPSI . Chem. Eur. J. 2008 , 14 , 2443 – 2452 .
  • Magill , A. M. ; McGuinness , D. S. ; Cavell , K. J. ; Britovsek , G. J. P. ; Gibson , V. C. ; White , A. J. P. ; Williams , D. J. ; White , A. H. ; Skelton , B. W. Palladium(II) complexes containing mono-, bi- and tridentate carbene ligands. Synthesis, characterisation and application as catalysts in C—C coupling reactions . J. Organomet. Chem. 2001 , 617–618 , 546 – 560 .
  • Knaggs , A. R. The biosynthesis of shikimate metabolites . Nat. Prod. Rep. 2003 , 20 , 119 – 136 .
  • Whiting , D. A. Natural phenolic compounds 1900–2000: a bird's eye view of a century's chemistry . Nat. Prod. Rep. 2001 , 18 , 583 – 606 .
  • (a) Maeda , S. ; Sudo , K. ; Miyamoto , Y. ; Takeda , S. ; Shinbo , M. ; Aburada , M. ; Ikeya , Y. ; Taguchi , H. ; Harada , M. Pharmacological studies on Schizandra fruits. II. Effects of constituents of Schizandra fruits on drug induced hepatic damage in rats . Yakugaku Zasshi 1982 , 102 , 579 – 588 ; (b) Kuo , Y. H. ; Huang , H. C. ; Yang Kuo , L. M. ; Chen , C. F. Novel C19 homolignans, taiwanschirin A, B, and cytotoxic taiwanschirin C, and a new C18 lignan, schizanrin A, from Schizandra arisanensis . J. Org. Chem. 1999 , 64 , 7023 – 7027 ; (c) Chen , D. F. ; Zhang , S. X. ; Kozuka , M. ; Sun , Q. Z. ; Feng , J. ; Wang , Q. ; Mukainaka , T. ; Nobukuni , Y. ; Tokuda , H. ; Nishino , H. ; Wang , H. K. ; Morris-Natschke , S. L. ; Lee , K. H. Interiotherins C and D, two new lignans from Kadsura interior and antitumor-promoting effects of related neolignans on Epstein–Barr virus activation . J. Nat. Prod. 2002 , 65 , 1242 – 1245 .
  • Chang , J. ; Reiner , J. ; Xie , J. Progress on the chemistry of dibenzocyclooctadiene lignans . Chem. Rev. 2005 , 105 , 4581 – 4609 .
  • Coleman , R. S. ; Gurrala , S. R. Asymmetric synthesis of the dibenzocyclooctadiene lignans Interiotherin A and Gomisin R . Org. Lett. 2005 , 7 , 1849 – 1852 .
  • Viciu , M. S. ; Kelly III , R. A. ; Stevens , E. D. ; Naud , F. ; Studer , M. ; Nolan , S. P. Synthesis, characterization, and catalytic activity of N-heterocyclic carbene (NHC) palladacycle complexes . Org. Lett. 2003 , 5 , 1479 – 1482 .
  • (a) Kakiuchi , F. ; Murai , S. Catalytic C–H/olefin coupling . Acc. Chem. Res. 2002 , 35 , 826 – 834 ; (b) Ritleng , V. ; Sirlin , C. ; Pfeffer , M. Ru-, Rh-, and Pd-catalyzed C–C bond formation involving C–H activation and addition on unsaturated substrates: Reactions and mechanistic aspects . Chem. Rev. 2002 , 102 , 1731 – 1770 .
  • Kano , T. ; Ohyabu , Y. ; Saito , S. ; Yamamoto , H. Asymmetric carbon–carbon coupling of phenols or anilines with aryllead triacetates . J. Am. Chem. Soc. 2002 , 124 , 5365 – 5373 .
  • Biftu , T. ; Hazra , B. G. ; Stevenson , R. Synthesis of (±)-deoxyschizandrin . J. Chem. Soc. Perkin Trans. I 1979 , 2276 – 2281 .
  • Herath , H. M. T. B. ; Priyadarshini , A. M. A. Lignans from Myristica dactyloides . Phytochemistry 1997, 44, 699–703.
  • (a) Hu , H. ; Wang , Z. Q. ; Liu , S. Y. ; Cheng , Y.-C. ; Lee , K.-H. Antitumor agents. 123. Synthesis and human DNA topoisomerase II inhibitory activity of 2′-chloro derivatives of etoposide and 4.beta.-(arylamino)-4′-O-demethylpodophyllotoxins . J. Med. Chem. 1992 , 35 , 866 – 871 ; (b) Whitman , S. ; Gezginci , M. ; Timmermann , B. N. ; Holman , T. R. Structure–activity relationship studies of nordihydroguaiaretic acid inhibitors toward soybean, 12-human, and 15-human lipoxygenase . J. Med. Chem. 2002 , 45 , 2659 – 2661 .
  • (a) Lian-Niang , L. ; Hung , X. ; Rui , T. Dibenzocyclooctadiene lignans from roots and stems of Kadsura coccinea . Planta Medica 1985 , 51 , 297 – 300 ; (b) Chattopadhyay , S. K. ; Rao , K. V. Chemistry of Saururus cernus IV: cyclooctadiene systems derived from austrobailignan-5 . Tetrahedron 1987 , 43 , 669 – 678 .

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