Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2011(13): 2073-2078
DOI: 10.1055/s-0030-1260045
DOI: 10.1055/s-0030-1260045
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
N-Heterocyclic Carbene Catalyzed Hydrophosphonylation of Aldehydes
Further Information
Received
21 February 2011
Publication Date:
13 May 2011 (online)
Publication History
Publication Date:
13 May 2011 (online)
Abstract
N-Heterocyclic carbene catalyzed Pudovik-type reaction of dimethyl trimethylsilyl phosphite and aldehydes for the construction of carbon-phosphorus bonds have been developed, providing α-hydroxyphosphonates in moderate to excellent yield.
Key words
N-heterocyclic carbene - Pudovik-type reaction - α-hydroxyphosphonates - aldehydes - C-P bond
- Supporting Information for this article is available online:
- Supporting Information
-
1a
Arduengo AJ.Harlow RL.Kline M. J. Am. Chem. Soc. 1991, 113: 361 - For recent reviews, see:
-
1b
Enders D.Balensiefer T. Acc. Chem. Res. 2004, 37: 534 -
1c
Zeitler K. Angew. Chem. Int. Ed. 2005, 44: 7506 -
1d
Enders D.Niemeier O.Henseler A. Chem. Rev. 2007, 107: 5606 -
1e
Marion N.Díez-González S.Nolan SP. Angew. Chem. Int. Ed. 2007, 46: 2988 -
1f
Nair V.Vellalath S.Babu BP. Chem. Soc. Rev. 2008, 37: 2691 -
2a
Ugai T.Tanaka S.Dokawa S. J. Pharm. Soc. Jpn. 1943, 63: 269 -
2b
Enders D.Kallfass U. Angew. Chem. Int. Ed. 2002, 41: 1743 -
2c
Enders D.Niemeier O.Balensiefer T. Angew. Chem. Int. Ed. 2006, 45: 1463 -
2d
Takikawa H.Hachisu Y.Bode JW.Suzuki K. Angew. Chem. Int. Ed. 2006, 45: 3492 -
2e
Enders D.Han J. Tetrahedron: Asymmetry 2008, 19: 1367 -
3a
Stetter H.Schreckenberg M. Angew. Chem. Int. Ed. Engl. 1973, 12: 81 -
3b
Kerr MS.Rovis T. Synlett 2003, 1934 -
3c
Kerr MS.Rovis T. J. Am. Chem. Soc. 2004, 126: 8876 -
3d
Nakamura T.Hara O.Tamura T.Makino K.Hamada Y. Synlett 2005, 155 -
3e
Mattson AE.Zuhl AM.Reynolds TE.Scheidt KA. J. Am. Chem. Soc. 2006, 128: 4932 -
3f
Dirocco DA.Oberg KM.Dalton DM.Rovis T. J. Am. Chem. Soc. 2009, 131: 10872 -
4a
Burstein C.Glorius F. Angew. Chem. Int. Ed. 2004, 43: 6205 -
4b
Sohn SS.Rosen EL.Bode JW. J. Am. Chem. Soc. 2004, 126: 14370 -
4c
Burstein C.Tschan S.Xie X.Glorius F. Synthesis 2006, 2418 -
4d
Nair V.Vellalath S.Poonoth M.Suresh E. J. Am. Chem. Soc. 2006, 128: 8736 -
4e
Chiang P.-C.Kaeobamrung J.Bode JW. J. Am. Chem. Soc. 2007, 129: 3520 -
4f
David BC.Raup DEA.Scheidt KA. J. Am. Chem. Soc. 2010, 132: 5345 -
5a
Nyce GW.Lamboy JA.Connor EF.Waymouth RM.Hedrick JL. Org. Lett. 2002, 4: 3587 -
5b
Grasa GA.Kissling RM.Nolan SP. Org. Lett. 2002, 4: 3583 -
5c
Grasa GA.Singh SM.Nolan SP. Synthesis 2004, 971 -
5d
Kano T.Sasaki K.Maruoka K. Org. Lett. 2005, 7: 1347 -
5e
Zeng T.-Q.Song G.-H.Li C.-J. Chem. Commun. 2009, 41: 6249 -
6a
Connor EF.Nyce GW.Myers M.Möck A.Hedrick JL. J. Am. Chem. Soc. 2002, 124: 914 -
6b
Nyce GW.Glauser T.Connor EF.Möck A.Waymouth RM.Hedrick JL. J. Am. Chem. Soc. 2003, 125: 3046 -
6c
Raynaud J.Ciolino A.Baceiredo A.Destarac M.Bonnette F.Kato T.Gnanou Y.Taton D. Angew. Chem. Int. Ed. 2008, 47: 5390 -
6d
Raynaud J.Ottou WN.Gnanou Y.Taton D. Chem. Commun. 2009, 6249 -
7a
Zhang YR.He L.Wu X.Shao PL.Ye S. Org. Lett. 2008, 10: 277 -
7b
Duguet N.Campbell CD.Slawin AMZ.Smith AD. Org. Biomol. Chem. 2008, 6: 1108 -
7c
He L.Lv H.Zhang Y.-R.Ye S. J. Org. Chem. 2008, 73: 8101 -
7d
Zhang Y.-R.Lv H.Zhou D.Ye S. Chem. Eur. J. 2008, 14: 8473 -
7e
Huang X.-L.He L.Shao P.-L.Ye S. Angew. Chem. Int. Ed. 2009, 48: 192 -
7f
Wang X.-N.Shao P.-L.Lv H.Ye S. Org. Lett. 2009, 11: 4029 -
7g
Lv H.You L.Ye S. Adv. Synth. Catal. 2009, 351: 2822 - For selected examples, see:
-
8a
Li G.-Q.Dai L.-X.You S.-L. Org. Lett. 2009, 11: 1623 -
8b
Hirano K.Biju AT.Piel I.Glorius F. J. Am. Chem. Soc. 2009, 131: 14190 -
8c
Riduan SN.Zhang Y.Ying JY. Angew. Chem. Int. Ed. 2009, 48: 3322 -
8d
Kawanaka Y.Phillips EM.Scheidt KA. J. Am. Chem. Soc. 2009, 131: 18028 -
8e
Raveendran AE.Paul RR.Suresh E.Nair V. Org. Biomol. Chem. 2010, 4: 901 -
8f
Biju AT.Wurz NE.Glorius F. J. Am. Chem. Soc. 2010, 132: 5970 -
8g
Vora HU.Rovis T. J. Am. Chem. Soc. 2010, 132: 2860 -
8h
Sarkar S.Grimme S.Studer A. J. Am. Chem. Soc. 2010, 132: 1190 -
8i
Gu L.Zhang Y. J. Am. Chem. Soc. 2010, 132: 914 - 9
Song J.Tan Z.Reeves JT.Gallou F.Yee NK.Senanayake CH. Org. Lett. 2005, 7: 2193 -
10a
Song JJ.Gallou F.Reeves JT.Tan ZL.Yee NK.Senanayake CH. J. Org. Chem. 2006, 71: 1273 -
10b
Suzuki Y.Abu Bakar MD.Muramatsu K.Sato M. Tetrahedron 2006, 62: 4227 -
10c
Suzuki Y.Muramatsu K.Yamauchi K.Morie Y.Sato M. Tetrahedron 2006, 62: 302 -
10d
Kano T.Sasaki K.Konishi T.Mii H.Maruoka K. Tetrahedron Lett. 2006, 47: 4615 -
10e
Fukuda Y.Maeda Y.Ishii S.Kondo K.Aoyama T. Synthesis 2006, 589 -
10f
Fukuda Y.Kondo K.Aoyama T. Synthesis 2006, 2649 -
10g
Fukuda Y.Maeda Y.Kondo K.Aoyama T. Synthesis 2006, 1937 -
10h
Fukuda Y.Maeda Y.Kondo K.Aoyama T. Chem. Pharm. Bull. 2006, 54: 397 - 11
Song J.Tan Z.Reeves JT.Yee NK.Senanayake CH. Org. Lett. 2007, 9: 1013 -
12a
Wu J.Sun X.Xia HG. Eur. J. Org. Chem. 2005, 4769 -
12b
Wu J.Sun XY.Ye SQ.Sun W. Tetrahedron Lett. 2006, 47: 4813 -
12c
Sun X.Ye S.Wu J. Eur. J. Org. Chem. 2006, 4787 -
12d
Liu YK.Li R.Yue L.Li BJ.Chen YC.Wu Y.Ding LS. Org. Lett. 2006, 8: 1521 - 13
Du G.-F.He L.Gu C.-Z.Dai B. Synlett 2010, 2513 - For reviews, see:
-
14a
Gröger H.Hammer B. Chem. Eur. J. 2000, 6: 943 -
14b
Kolodiazhnyi OI. Tetrahedron: Asymmetry 2005, 16: 3295 -
14c
Kolodiazhnyi OI. Russ. Chem. Bull. 2006, 75: 227 -
15a
Atherton FR.Hassall CH.Lambert RW. J. Med. Chem. 1986, 29: 29 -
15b
Hammerschmidt F. Angew. Chem. Int. Ed. Engl. 1994, 33: 341 ; Angew. Chem. 1994, 106, 334 -
16a
Jennings LJ.Macchia M.Parkin A. J. Chem. Soc., Perkin Trans. 1 1992, 2197 -
16b
Huang J.Chen R. Heteroat. Chem. 2000, 11: 480 - 17
Lavielle G.Hautefaye P.Schaeffer C.Boutin JA.Cudennec CA.Pierré A. J. Med. Chem. 1991, 34: 1998 -
18a
Natchev IA. Liebigs Ann. Chem. 1988, 861 -
18b
Mao MK.Franz JE. Synthesis 1991, 920 - 19
Emsley J.Hall D. The Chemistry of Phosphorus Harper and Row; London: 1976. p.494 - For reviews, see:
-
20a
Merino P.López EM.Herrera RP. Adv. Synth. Catal. 2008, 350: 1195 -
20b
Ma J.-A. Chem. Soc. Rev. 2006, 35: 630 -
20c
Kolodiazhnyi OI. Tetrahedron: Asymmetry 1998, 9: 1279 -
20d
Pudovik AN.Konovalova IV. Synthesis 1979, 81 - For recent examples of hydrophosphonylation reactions, see:
-
20e
Suyama K.Sakai Y.Matsumoto K.Saito B.Katsuki T. Angew. Chem. Int. Ed. 2010, 49: 797 -
20f
Nakamura S.Hayashi M.Hiramatsu Y.Shibata N.Funahashi Y.Toru T.
J. Am. Chem. Soc. 2009, 131: 18240 -
20g
Uraguchi D.Ito T.Ooi T. J. Am. Chem. Soc. 2009, 131: 3836 -
20h
Zhou X.Liu Y.Chang L.Zhao J.Shang D.Liu X.Lin L.Feng X.-M. Adv. Synth. Catal. 2009, 351: 2567 -
20i
Akiyama T.Morita H.Bachu P.Mori K.Yamanaka M.Hirata T. Tetrahedron 2009, 65: 4950 -
20j
Noronha RG.Costa PJ.Romaõ CC.Fernandes AC. Organometallics 2009, 28: 6206 -
20k
Wang F.Liu X.-H.Cui X.Xiong Y.Zhou X.Feng X.-M. Chem. Eur. J. 2009, 15: 589 -
20l
Zhou X.Liu XH.Yang X.Shang DJ.Xin JG.Feng X.-M. Angew. Chem. Int. Ed. 2008, 47: 392 -
20m
Yang F.Zhao DB.Lan JB.Xi PH.Yang L.Xiang SH.You J. Angew. Chem. Int. Ed. 2008, 47: 5646 -
20n
Tajbakhsh M.Heydari A.Khalilzadeh M.-A.Lakouraj M.-M.Zamenian B.Khaksar S. Synlett 2007, 2347 -
21a
Hatano M.Suzuki S.Takagi E.Ishihara K. Tetrahedron Lett. 2009, 50: 3171 -
21b
Das B.Balasubramanyam P.Krishnaiah M.Veeranjaneyulu B.Reddy GC. J. Org. Chem. 2009, 74: 4393 - 22
Arduengo AJ.Krafczyk R.Schmutzler R. Tetrahedron 1999, 55: 14523 - 23
Ghadwal RS.Sen SS.Roesky HW.Tavcar G.Merkel S.Stalke D. Organometallics 2009, 28: 6347 - 24
Kerr MS.de Alaniz JR.Rovis T. J. Org. Chem. 2005, 70: 5725 -
25a
Jacques J.Leclercq M.Brienne M.-J. Tetrahedron 1981, 37: 1727 -
25b
Devitt P.-G.Mitchell M.-C.Weetman J.-M.Taylor R.-J.Kee T.-P. Tetrahedron: Asymmetry 1995, 6: 2039 -
25c
Azizi N.Saidi M.-R. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178: 1255 -
25d
Elio N.Antonella R. Gazz. Chim. Ital. 1989, 119: 19