Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 2
1,131
Views
12
CrossRef citations to date
0
Altmetric
Original Articles

Pd-Catalyzed Reduction of Aldehydes to Alcohols Using Formic Acid as the Hydrogen Donor

, , , , , & show all
Pages 280-288 | Received 13 Apr 2013, Published online: 29 Oct 2013

REFERENCES

  • (a) Hudlicky , M. Reductions in Organic Chemistry, , 2nd ed. ; ACS : Washington , DC , 1996 ; (b) Rylander , P. N. Hydrogenation Methods ; Academic : New York , 1985 ; (c) Zassinovich , G. ; Mestroni , G. Asymmetric hydrogen transfer reactions promoted by homogeneous transition metal catalysts. Chem. Rev. 1992, 92, 1051–1069 ; (d) Moore , J. C. ; Pollard , D. J. ; Kosjek , B. ; Devine , P. N. Advances in the enzymatic reduction of ketones. Acc. Chem. Res. 2007, 40, 1412–1419 ; (e) González , S. D. ; Marion , N. ; Nolan , S. P. N-Heterocyclic carbenes in late transition-metal catalysis. Chem. Rev. 2009, 109, 3612–3676 ; (f) Alonso , F. ; Riente , P. ; Yus , M. Nickel nanoparticles in hydrogen transfer reactions. Acc. Chem. Res. 2011, 44, 379–391 ; (g) Shang , G. ; Li , W. ; Zhang , X. M. Transition metal–catalyzed homogeneous asymmetric hydrogenation . In Handbook of Catalytic Asymmetric Synthesis , I. Ojima (Eds.); John Wiley & Sons : Hoboken , NJ , 2010 .
  • (a) Luche , J, L. Lanthanides in organic chemistry, 1: Selective 1,2-reductions of conjugated ketones. J. Am. Chem. Soc. 1978 , 100 , 2226 – 2227 ; (b) Luche , J. L. ; Rodriguez-Hahn , L. ; Crabbé , P. Reduction of natural enones in the presence of cerium trichloride . J. Chem. Soc., Chem. Commun. 1978 , 14 , 601 – 602 ; (c) Gemai , A. L ; Luche , J. L. Lanthanoids in organic synthesis, 6: Reduction of α-enones by sodium borohydride in the presence of lanthanoid chlorides: Synthetic and mechanistic aspects . J. Am. Chem. Soc. 1981 , 103 , 5454 – 5459 .
  • (a) Felkin , E. ; Sarda , P. Reductive cleavage of allylic alcohols ethers, or acetates to olefins . Org. Synth. 1988 , 6 , 769 – 769 ; (b) Barnier , J. P. ; Champion , J. ; Conia , J. M. Cyclopropanecarboxaldehyde . Org. Synth. 1990 , 7 , 129 – 129 .
  • (a) Hattori , K. ; Sajiki , H. ; Hirota , K. Chemoselective control of hydrogenation among aromatic carbonyl and benzyl alcohol derivatives using Pd/C(en) catalyst. Tetrahedron 2001, 57, 4817–4824; (b) Ohkuma , T. ; Ooka , H. ; Ikariya , T. ; Noyori , R. Preferential hydrogenation of aldehydes and ketones. J. Am. Chem. Soc. 1995, 117, 10417–10418; (c) Ohkuma , T. ; Koizumi , M. ; Ikehira , H. ; Yokozama , T. ; Noyori , R. Selective hydrogenation of benzophenones to benzhydrols: Asymmetric synthesis of unsymmetrical diarylmethanols. Org. Lett. 2000, 2, 659–662; (d) Ohkuma , T. ; Hattori , T. ; Ooka , H. ; Inoue , T. ; Noyori , R. BINAP/1,4-diamine-ruthenium(II) complexes for efficient asymmetric hydrogenation of 1-tetralones and analogues. Org. Lett. 2004, 6, 2681–2683; (e) Ohkuma , T. ; Tsutsumi , K. ; Utsumi , N. ; Arai , N. ; Noyori , R. ; Murata , K. Asymmetric hydrogenation of r-chloro aromatic ketones catalyzed by η6-arene/TsDPEN-ruthenium(II) complexes. Org. Lett. 2007, 9, 255–257.
  • (a) Sandoval , C. A ; Ohkuma , T. K. ; Noyori , R. Mechanism of asymmetric hydrogenation of ketones catalyzed by BINAP/1,2-diamine-ruthenium(II) complexes . J. Am. Chem. Soc. 2003 , 125 , 13490 – 13503 ; (b) Sandoval , C. A. ; Noyori , R. The hydrogenation/transfer hydrogenation network in asymmetric reduction of ketones catalyzed by [RuCl2(BINAP)(PICA)] complexes . Chem. Asian J. 2008 , 3 , 1801 – 1810 ; (c) Lin , Y. H. ; Zhou , Y. G. ; Shi , Q. X. ; Ding , K. L. ; Noyori , R. An efficient diphosphine/hybrid-amine combination for ruthenium(II)-catalyzed asymmetric hydrogenation of aryl ketones . Adv. Synth. Catal. 2011 , 353 , 495 – 500 .
  • (a) Meerwein , H. ; Schmidt , R. New method for the reduction of aldehydes and ketones . Justus Liebigs Ann. Chem. 1925 , 444 , 221 – 238 ; (b) Ponndorf , W. The reversible exchange of oxygen between aldehydes or ketones on the one hand and primary or secondary alcohols on the other hand . Angew. Chem. 1926 , 39 , 138 – 146 ; (c) Verley , M. The exchange of functional groups between two molecules: The passage of ketones to alcohols and the reverse . Bull. Soc. Chim. Fr. 1925 , 37 , 871 – 874 .
  • (a) Ooi , T. ; Miura , T. ; Maruoka , K. Highly efficient, catalytic Meerwein–Ponndorf–Verley reduction with a novel bidentate aluminum catalyst . Angew. Chem. Int. Ed. 1998 , 37 , 2347 – 2349 ; (b) Ooi , T. ; Ichikaw , H. ; Maruoka , K. Practical approach to the Meerwein-Ponndorf-Verley reduction of carbonyl substrates with new aluminum catalysts . Angew. Chem. Int. Ed. 2001 , 40 , 3610 – 3612 ; (c) Ooi , T. ; Miura , T. ; Itagaki , Y. ; Ichikawa , H. ; Maruoka , K. Bronsted acid catalysts other than phosphoric acids . Synthesis 2002 , 2 , 279 – 291 ; (d) Camphbell , J. E. ; Zhou , H. Y. ; Nguyen , S. T. Enantioselective synthesis of kedarcidin chromophore aglycon in differentially protected form . Angew. Chem. Int. Ed. 2002 , 41 , 1062 – 1064 ; (e) Yin , J. J. ; Huffman , M. A. ; Conrad , K. M. ; Armstrong , J. D. Highly diastereoselective catalytic Meerwein–Ponndorf–Verley reductions . J. Org. Chem. 2006 , 71 , 840 – 843 .
  • For examples of Pd-catalyzed hydrogen transfer reduction of aldehydes and ketones, see (a) Baidossi , M. ; Joshi , A. V. ; Mukhopadhyay , S. ; Sasson , Y. Pd/C-catalyzed transfer-hydrogenation of benzaldehydes to benzyl alcohols using potassium formate as the selective hydrogen donor . Synth. Commun. 2004 , 34 , 643 – 650 ; (b) Cano , R. ; Yus , M. ; Ramón , D. J. Impregnated palladium on magnetite as catalyst for multicomponent reductive amination reactions and other related reducing processes . Tetrahedron 2011 , 67 , 8079 – 8085 .
  • For examples of Fe-catalyzed hydrogen transfer reduction of aldehydes and ketones, see (a) Nishiyama , S. ; Furuta , A. An iron-catalysed hydrosilylation of ketones . Chem. Commun. 2007 , 7 , 760 – 762 ; (b) Shaikh , N. S. ; Junge , K. ; Beller , M. convenient and general iron-catalyzed hydrosilylation of aldehydes . Org. Lett. 2007 , 9 , 5429 – 5432 ; (c) Jiang , F. ; Bézier , D. ; Sortais , J. B. ; Darcel , C. N-Heterocyclic carbene piano-stool iron complexes as efficient catalysts for hydrosilylation of carbonyl derivatives. Adv. Synth. Catal. 2011 , 353 , 239 – 244 ; (d) Misal Castro , L. C. ; Bézier , D. ; Sortais , J. B. ; Darcel , C. Iron dihydride complex as the pre-catalyst for efficient hydrosilylation of aldehydes and ketones under visible light activation . Adv. Synth. Catal. 2011 , 353 , 1279 – 1284 ; (e) Zheng , J. X. ; Misal Castro , L. C. ; Darcel , C. ; Sortais , J. B. Iron piano-stool phosphine complexes for catalytic hydrosilylation reaction . Inorg. Chim. Acta 2012 , 380 , 301 – 307 ; (f) Bézier , D. ; Jiang , F. ; Sortais , J. B. ; Darcel , C. Cyclopentadienyl–NHC iron complexes for solvent-free catalytic hydrosilylation of aldehydes and ketones . Eur. J. Inorg. Chem. 2012 , 1333 – 1337 .
  • For an example of Ni-catalyzed hydrogen transfer reduction of aldehydes and ketones, see Bheeter , L. P. ; Henrion , M. ; Brelot , L. ; Darcel , C. ; Chetcuti , M. J. ; Sortais , J. B. ; Ritleng , V. Hydrosilylation of aldehydes and ketones catalyzed by an N-heterocyclic carbene–nickel hydride complex under mild conditions . Adv. Synth. Catal. 2012 , 354 , 2619 – 2624 .
  • For examples of Ru-catalyzed hydrogen-transfer reduction of aldehydes and ketones, see (a) Haack , K. J. ; Hashiguchi , S. ; Fujii , A. ; Ikariya , T. ; Noyori , R. The catalyst precursor, catalyst, and intermediate in the RuII-promoted asymmetric hydrogen transfer between alcohols and ketones. Angew. Chem., Int. Ed. 1997, 36, 285–288; (b) Yamakawa , M. ; Ito , H. ; Noyori , R. The metal–ligand bifunctional catalysis: A theoretical study on the ruthenium(II)-catalyzed hydrogen transfer between alcohols and carbonyl compounds. J. Am. Chem. Soc. 2000, 122, 1466–1478; (c) Munihiko , M. ; Okano , K. ; Miyagi , M. ; Iwane , H. ; Noyori , R. ; Ikariya , T. A practical stereoselective synthesis of chiral hydrobenzoins via asymmetric transfer hydrogenation of benzils. Org. Lett. 1999, 1, 1119–1121; (d) Yamada , I. ; Noyori , R. Asymmetric transfer hydrogenation of benzaldehydes. Org. Lett. 2000, 2, 3425–3427.
  • (a) Wiener , H. ; Zaidman , B. ; Sasson , Y. Storage of energy by solutions of alkali formate salts . Solar Energy 1989 , 43 , 291 – 296 ; (b) Wiener , H. ; Zaidman , B. ; Sasson , Y. Application of aqueous formate salts as hydrogen donors in reduction processes: A techno-economic comparison with pressurized and electrically generated hydrogen gas . Int. J. Hydrogen Energy 1989 , 14 , 365 – 370 ; (c) Noyori , R. ; Hashiguchi , S. Asymmetric transfer hydrogenation catalyzed by chiral ruthenium complexes . Acc. Chem. Res. 1997 , 30 , 97 – 102 .
  • Shen , R. S. ; Chen , T. Q. ; Zhao , Y. L. ; Qiu , R. H. ; Zhou , Y. B. ; Yin , S. F. ; Wang , X. B. ; Goto , M. ; Han , L. B. Facile regio- and stereoselective hydrometalation of alkynes with a combination of carboxylic acids and group 10 transition metal complexes: Selective hydrogenation of alkynes with formic acid . J. Am. Chem. Soc. 2011 , 133 , 17037 – 17044 .

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.