Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 2
948
Views
6
CrossRef citations to date
0
Altmetric
Original Articles

Unexpected Transformation of Aldehydes into Benzoins with Copper(I)/Samarium

, , , &
Pages 259-266 | Received 11 Mar 2013, Published online: 29 Oct 2013

REFERENCES

  • (a) Amblard , F. ; Cho , J. H. ; Schinazi , R. F. Chem. Rev. 2009 , 109 , 4207 – 4220 ; (b) Alexakis , A. ; Bäckvall , J. E. ; Krause , N. ; Pämies , O. ; Diéguez , M. Chem. Rev. 2008 , 108 , 2796 – 2823 ; (c) Daugulis , O. ; Do , H.-Q. ; Shabashov , D. Acc. Chem. Res. 2009 , 42 , 1074 – 1086 ; (d) Zhang , C. ; Tang , C. ; Jiao , N. Chem. Soc. Rev. 2012 , 41 , 3464 – 3484 .
  • (a) Gilman , H. ; Jones , R. G. ; Woods , L. A. J. Org. Chem. 1952 , 17 , 1630 – 1634 ; (b) Yang , C.-T. ; Zhang , Z.-Q. ; Liang , J. ; Liu , J.-H. ; Lu , X.-Y. ; Chen , H.-H. ; Liu , L. J. Am. Chem. Soc. 2012 , 134 , 11124 – 11127 ; (c) Lipshutz , B. H. ; Huang , S. ; Leong , W. W. Y. ; Zhong , G. ; Isley , N. A. J. Am. Chem. Soc. 2012 , 134 , 19985 – 19988 ; (d) Tarwade , V. ; Liu , X. ; Yan , N. ; Fox , J. M. J. Am. Chem. Soc. 2009 , 131 , 5382 – 5383 ; (e) Pierce , C. J. ; Nguyen , M. ; Larsen , C. H. Angew. Chem. Int. Ed. 2012 , 51 , 12289 – 12292 ; (f) Kim , Y. W. ; Niphakis , M. J. ; Georg , G. I. J. Org. Chem. 2012 , 77 , 9496 – 9503 ; (g) Liu , X.-Y. ; Gao , P. ; Shen , Y.-W. ; Liang , Y.-M. Org. Lett. 2011 , 13 , 4196 – 4199 ; (h) You , J. ; Wang , Z. ; Li , K. ; Zhao , D. ; Lan , J. Angew. Chem. Int. Ed. 2011 , 50 , 5365 – 5369 ; (i) Sun , M. ; Shen , G. ; Bao , W. Adv. Synth. Catal. 2012 , 354 , 3468 – 3474 .
  • For some recent references on Cu(III) species and reactions involving Cu(III) intermediates, see (a) Gärtner , T. ; Henze , W. ; Gschwind , R. M. J. Am. Chem. Soc. 2007 , 129 , 11362 – 11363 ; (b) He , C. ; Guo , S. ; Huang , L. ; Lei , A. J. Am. Chem. Soc. 2010 , 132 , 8273 – 8275 ; (c) Yang , L. ; Lu , Z. ; Stahl , S. S. Chem. Commun. 2009 , 6460 – 6462 ; (d) Zhao , B. ; Peng , X. ; Zhu , Y. ; Ramirez , T. A. ; Cornwall , R. G. ; Shi , Y. J. Am. Chem. Soc. 2011 , 129 , 20890 – 20900 ; (e) King , A. E. ; Brunold , T. C. ; Stahl , S. S. J. Am. Chem. Soc. 2009 , 131 , 5044 – 5045 .
  • (a) Nicolaou , K. C. ; Ellery , S. P. ; Chen , J. S. Angew. Chem. Int. Ed. 2009 , 48 , 7140 – 7165 ; (b) Procter , D. J. ; Flowers II , R. A. ; Skrydstrup , T. Organic Synthesis Using Samarium Diiodide: A Practical Guide; Royal Society of Chemistry: London, 2009 ; (c) Flowers II , R. A. Synlett 2008 , 1427 – 1439 ; (d) Edmonds , D. J. ; Johnston , D. ; Procter , D. J. Chem. Rev. 2004 , 104 , 3371 – 3404 ; (e) Szostak , M. ; Spain , M. ; Procter , D. J. J. Org. Chem. 2012 , 77 , 3049 – 3059 .
  • For review for the use of metallic samarium, see Banik , B. K. Eur. J. Org. Chem. 2002 , 2431 – 2444 .
  • (a) Ogawa , A. ; Takami , N. ; Sekiguchi , M. ; Ryu , I. ; Kambe , N. ; Sonoda , N. J. Am. Chem. Soc. 1992 , 114 , 8729 – 8730 ; (b) Kamochi , Y. ; Kudo , T. Chem. Pharm. Bull. 1994 , 42 , 402 – 404 ; (c) Banik , B. K. ; Mukhopadhyay , C. ; Venkatraman , M. S. ; Becker , F. F. Tetrahedron Lett. 1998 , 39 , 7243 – 7246 ; (d) Ghatak , A. ; Becker , F. F. ; Banik , B. K. Tetrahedron Lett. 2000 , 41 , 3793 – 3796 ; (e) Talukdar , S. ; Fang , J.-M. J. Org. Chem. 2001 , 66 , 330 – 333 .
  • For example: (a) Liu , Y. ; Zhang , F. ; Qi , Y. ; Zhang , Y. ; Zhang , S. Eur. J. Org. Chem. 2008 , 5470 – 5476 ; (b) Liu , Y. ; Li , Y. ; Qi , Y. ; Wan , J. Synthesis 2010 , 4188 – 4192 ; (c) Liu , Y. ; Xu , X. ; Zhang , Y. Synlett. 2004 , 445 – 448 ; (d) Liu , Y. ; Zhang , Y. Tetrahedron Lett. 2004 , 45 , 1295 – 1298 ; (e) Liu , Y. ; Zhang , Y. Tetrahedron 2003 , 59 , 8429 – 8437 ; (f) Liu , Y. ; Xu , X. ; Zhang , Y. Tetrahedron 2004 , 60 , 4867 – 4873 .
  • (a) Molander , G. A. ; Kenny , C. J. Am. Chem. Soc. 1989 , 111 , 8236 – 8246 ; (b) Hélion , F. ; Namy , J.-L. J. Org. Chem. 1999 , 64 , 2944 – 2946 .
  • (a) Breslow , R. J. Am. Chem. Soc. 1958, 80, 3719–3726; (b) Miyashita , A. ; Suzuki , Y. ; Iwamoto , K.-I. ; Higashino , T. Chem. Pharm. Bull. 1994, 42, 2633–2635; (c) Iwamoto , K.-I. ; Kimura , H. ; Oike , M. ; Sato , M. Org. Biomol. Chem. 2008, 6, 912–915.
  • (a) Burwell Jr. , R. L. J. Am. Chem. Soc. 1948 , 70 , 2865 – 2869 ; (b) Tao , S.-X. ; Wang , G.-C. ; Bu , X.-H. J. Phys. Chem. B 2006 , 110 , 26045 – 26054 ; (c) Chary , K. V. R. ; Sagar , G. V. ; Srikanth , C. S. ; Rao , V. V. J. Phys. Chem. B 2007 , 111 , 543 – 550 ; (d) Li , L. ; Sarjeant , A. A. N. ; Karlin , K. D. Inorg. Chem. 2006 , 45 , 7160 – 7172 ; (e) Cao , H. ; Jiang , H.; Yao W. ; Liu , X. Org. Lett. 2009 , 11 , 1931 – 1933 .
  • (a) Gampp , H. ; Haspra , D. ; Spieler , W. ; Zuberbühler , D. Helv. Chim. Acta. 1984 , 67 , 1019 – 1025 ; (b) Hatanaka , Y. ; Imamoto , T. ; Yokoyama , M. Tetrahedron Lett. 1983 , 24 , 2399 – 2400 .

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.