Aryl Nitro Reduction with Iron Powder or Stannous Chloride under Ultrasonic Irradiation

References

• Wang , L. , Li , P. , Wu , Z. , Yan , J. , Wang , M. and Ding , Y. 2003 . Reduction of nitroarenes to aromatic amines with nanosized activated metallic iron powder in water . Synthesis , 13 : 2001 – 2004 .
   Web of Science ®Google Scholar
• Herepoulos , G. A. , Georgakopoulos , S. and Steele , B. R. 2005 . High intensity ultrasound‐assisted reduction of sterically demanding nitroaromatics . Tetrahedron Lett. , 46 : 2469 – 2473 .
   Web of Science ®Google Scholar
• Nagaraja , D. and Pasha , M. A. 1999 . Reduction of aryl nitro compounds with aluminium/NH4Cl: Effect of ultrasound on the rate of the reaction . Tetrahedron Lett. , 40 : 7855 – 7856 .
   Web of Science ®Google Scholar
• Pyo , S. H. and Han , B. H. 1995 . Reduction of nitroarenes by activated metals . Bull. Korean Chem. Soc. , 16 : 181 – 183 .
   Web of Science ®Google Scholar
• Nomura , K. 1998 . Transition metal catalyzed hydrogenation or reduction in water . J. Mol. Catal. , 130 : 1 – 28 .
   Web of Science ®Google Scholar
• Downing , R. S. , Kunkeler , P. J. and van Bekkum , H. 1997 . Catalytic syntheses of aromatic amines . Catal. Today , 37 : 121 – 136 .
   Web of Science ®Google Scholar
• Boix , C. and Poliakoff , M. 1999 . Selective reductions of nitroarenes to anilines using metallic zinc in near‐critical water . J. Chem. Soc., Perkin Trans. 1 , : 1487 – 1490 .
   Google Scholar
• Liu , Y. , Lu , Y. , Prashad , M. , Repic , O. and Blacklock , T. J. 2005 . A practical and chemoselective reduction of nitroarenes to anilines using activated iron . Adv. Synth. Catal. , 347 : 217 – 219 .
   Web of Science ®Google Scholar
• Hazlet , S. E. and Dornfeld , C. A. 1944 . The reduction of aromatic nitro compounds with activated iron . J. Am. Chem. Soc. , 66 : 1781 – 1782 .
   Google Scholar
• Bellamy , F. D. and Ou , K. 1984 . Selective reduction of aromatic nitro compounds with stannous chloride in nonacidic nonaqueous medium . Tetrahedron Lett. , 25 : 839 – 842 .
   Web of Science ®Google Scholar
• Guay , V. and Brassard , P. 1987 . The regiospecific synthesis of the A and B rings of phomazarin . J. Heterocycl. Chem. , 24 : 1649 – 1652 .
   Web of Science ®Google Scholar
• Owsley , D. C. and Bloomfield , J. J. 1977 . The reduction of nitroarenes with iron/acetic acid . Synthesis , : 118 – 120 .
   Web of Science ®Google Scholar
• Nuchter , M. , Ondruschka , B. , Jungnickel , A. and Muller , U. 2000 . Organic processes initiated by non‐classical energy sources . J. Phys. Org. Chem. , 13 : 579 – 586 .
   Web of Science ®Google Scholar
• Luche , J. L. 1998 . Synthetic Organic Sonochemistry New York : Plenum Press .
   Google Scholar
• Rai , G. , Jeong , J. M. , Lee , Y. S. , Kim , H. W. , Lee , D. S. , Chung , J. K. and Lee , M. C. 2005 . Ionic liquid mediated efficient reduction of nitroarenes using stannous chloride under sonication . Tetrahedron Lett. , 46 : 3987 – 3990 .
   Web of Science ®Google Scholar
• Hung , H. M. , Ling , F. H. and Hoffmann , M. R. 2000 . Kinetics and mechanism of the enhanced reductive degradation of nitrobenzene by elemental iron in the presence of ultrasound . Environ. Sci. Technol. , 34 : 1758 – 1763 .
   Web of Science ®Google Scholar
• Han , B. H. , Shin , D. H. and Cho , S. Y. 1985 . Organic sonochemistry: Ultrasonic acceleration of the reduction of aromatic nitro compounds with hydrazine‐iron in the presence of activated carbon . Bull. Korean Chem. Soc. , 6 : 320
   Web of Science ®Google Scholar
• Pasha , M. A. and Jayashankara , V. P. 2005 . Reduction of arylnitro compounds to azoarenes and/or arylamines by Al/NaOH in methanol under ultrasonic conditions . Ultrason. Sonochem. , 12 : 433 – 435 .
   PubMed Web of Science ®Google Scholar
• Blaser , H.‐U. , Malan , C. , Pugin , B. , Spindler , F. , Steiner , H. and Studer , M. 2003 . Selective hydrogenation for fine chemicals: Recent trends and new developments . Adv. Synth. Catal. , 345 : 103 – 151 .
   Web of Science ®Google Scholar
• Radziejewski , C. , Ghosh , S. and Kaiser , E. T. 1987 . The synthesis of two strongly electron deficient flavin analogs . Heterocycles , 26 : 1227 – 1238 .
   Web of Science ®Google Scholar
• Simpson , J. C. E. , Atkinson , C. M. , Schofield , K. and Stephenson , O. 1945 . o‐Amino‐ketones of the acetophenone and benzophenone types . J. Chem. Soc. , : 646 – 657 .
   Web of Science ®Google Scholar
• Viswanathan , N. and Patankar , S. J. 1985 . Synthesis of 5,5′‐dibromo‐8,8′‐dihydroxy‐7,7′‐biquinoline . Indian J. Chem. , 24B : 1284 – 1285 .
   Google Scholar
• Baindur , N. , Chadha , N. and Player , M. R. 2003 . Solution‐phase synthesis of a library of 3,5,7‐trisubstituted 3H‐[1,2,3]triazole[4,5‐d]pyrimidines . J. Comb. Chem. , 5 : 653 – 659 .
   Google Scholar
• Lee , D.‐Y. and Hartwig , J. F. 2005 . Zinc trimethylsilylamide as a mild ammonia equivalent and base for the amination of aryl halides and triflates . Org. Lett. , 7 : 1169 – 1172 .
   PubMed Web of Science ®Google Scholar
• Wolter , M. , Nordmann , G. , Job , G. E. and Buchwald , S. L. 2002 . Copper‐catalysed coupling of aryl iodides with aliphatic alcohols . Org. Lett. , 4 : 973 – 976 .
   PubMed Web of Science ®Google Scholar
• Pal , M. , Parasuraman , K. and Yeleswarapu , K. R. 2003 . Palladium‐catalysed cleavage of O/N‐propargyl protecting groups in aqueous media under copper‐free condition . Org. Lett. , 5 : 349 – 452 .
   PubMed Web of Science ®Google Scholar
• Malamas , M. S. , Manas , E. S. , McDevitt , R. E. , Gunawan , I. , Xu , Z. B. , Collini , M. D. , Miller , C. P. , Dihn , T. , Henderson , R. A. , Keith , J. C. Jr. and Harris , H. A. 2004 . Design and synthesis of aryl diphenolic azoles as potent and selective estrogen receptor‐β ligands . J. Med. Chem. , 47 : 5021 – 5040 .
   PubMed Web of Science ®Google Scholar
• Krolski , M. E. , Renaldo , A. F. , Rudisill , D. E. and Stille , J. K. 1988 . Palladium‐catalysed coupling of 2‐bromoanilines with vinylstannanes: A regiocontrolled synthesis of substituted indoles . J. Org. Chem. , 53 : 1170 – 1176 .
   Web of Science ®Google Scholar