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Volumn 653, Issue 1-2, 2002, Pages 252-260

Palladium-catalyzed cross-coupling reaction of anilinium hypophosphite with alkenyl bromides and triflates: Application to the synthesis of GABA analogs

(2) Dumond, Yves R a Montchamp, Jean Luc a

a TEXAS CHRISTIAN UNIVERSITY (United States)

Author keywords

Anilinium hypophosphite; Cross coupling; GABA analogs; Palladium catalysis; Phosphinic acid

Indexed keywords

4 AMINOBUTYRIC ACID DERIVATIVE; 4 AMINOBUTYRIC ACID RECEPTOR; ALKENYL GROUP; ANILINE DERIVATIVE; ARECAIDINE; BENZENE; BROMINE DERIVATIVE; CARBON; PALLADIUM; PHOSPHINIC ACID DERIVATIVE; PHOSPHITE; PHOSPHORUS; PHOSPHORUS ACID DERIVATIVE; TETRAHYDROFURAN; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPETITION; CONTROLLED STUDY; METHODOLOGY; SYNTHESIS;

EID: 0036643423 PISSN: 0022328X EISSN: None Source Type: Journal
DOI: 10.1016/S0022-328X(02)01271-8 Document Type: Article

Times cited : (38)

References (67)

1
- 0035812795
- (2001) J. Org. Chem , vol.66 , pp. 6745
- Deprèle, S.¹ Montchamp, J.-L.²

2
- 0036471109
- (2002) Organomet. Chem , vol.643 , Issue.644 , pp. 154
- Deprèle, S.¹ Montchamp, J.-L.²

3
- 0035941499
- (2001) J. Am. Chem. Soc , vol.123 , pp. 510
- Montchamp, J.-L.¹ Dumond, Y.R.²

4
- 0001281090
- For examples of transition metal catalyzed P-C bond formation via cross-coupling
- (1998) J. Org. Chem , vol.63 , pp. 3463
- Martorell, G.¹ Garcías, X.² Janura, M.³ Saá, J.M.⁴

5
- 0000497218
- (1990) J. Org. Chem , vol.55 , pp. 5033
- Hinkle, R.J.¹ Stang, P.J.² Kowalski, M.H.³

6
- 33845281574
- (1987) J. Org. Chem , vol.52 , pp. 748
- Tunney, S.E.¹ Stille, J.K.²

7
- 0000200137
- (1980) Tetrahedron Lett , vol.21 , pp. 3595
- Hirao, T.¹ Masunaga, T.² Oshiro, Y.³ Agawa, T.⁴

8
- 0001412847
- (1982) Bull. Chem. Soc. Jpn , vol.55 , pp. 909
- Hirao, T.¹ Masunaga, T.² Yamada, N.³

9
- 0021126349
- (1984) Synthesis , pp. 778
- Xu, Y.¹ Zhang, J.²

10
- 85005466990
- (1983) Synthesis , pp. 377
- Xu, Y.¹ Li, Z.² Xia, J.³ Guo, H.⁴ Huang, Y.⁵

11
- 0021208856
- (1984) Synthesis , pp. 781
- Xu, Y.¹ Li, Z.² Xia, J.³ Guo, H.⁴ Huang, Y.⁵

12
- 0002385018
- (1986) Synthesis , pp. 240
- Xu, Y.¹ Li, Z.²

13
- 0003005047
- (1986) Synthesis , pp. 691
- Xu, Y.¹ Xia, J.² Guo, H.³

14
- 37049087486
- (1986) J. Chem. Soc. Chem. Commun , pp. 1606
- Xu, Y.¹ Zhang, J.²

15
- 0001677051
- (1989) Tetrahedron Lett , vol.30 , pp. 949
- Xu, Y.¹ Wej, H.² Zhang, J.³ Huang, G.⁴

16
- 0026619378
- (1992) Synthesis , pp. 1255
- Lei, H.¹ Stoakes, M.S.² Schwabacher, A.W.³

17
- 12044251218
- (1993) J. Am. Chem. Soc , vol.115 , pp. 6995
- Schwabacher, A.W.¹ Zhang, S.² Davy, W.³

18
- 0028067621
- (1994) J. Org. Chem , vol.59 , pp. 4206
- Lei, H.¹ Stoakes, M.S.² Herath, K.P.B.³ Lee, J.⁴ Schwabacher, A.W.⁵

19
- 0000419694
- (1970) Tetrahedron , vol.26 , pp. 5529
- Tavs, P.¹ Wetkamp, H.²

20
- 0033555694
- (1999) Tetrahedron Lett , vol.40 , pp. 569
- Kazankova, M.A.¹ Trostyanskaya, I.G.² Lutsenko, S.V.³ Beletskaya, I.P.⁴

21
- 0025017980
- (1990) Tetrahedron Lett , vol.31 , pp. 6321
- Kurtz, L.¹ Lee, G.² Morgans, D.³ Waldyke, M.J.⁴ Ward, T.⁵

22
- 0033001928
- (1999) Synlett , vol.6 , pp. 721
- Zhong, P.¹ Huang, X.² Xiong, Z.-X.³

23
- 37049095565
- (1983) J. Chem. Soc. Chem. Commun , pp. 1055
- Fiaud, J.-C.¹

24
- 0026734927
- (1992) Synth. Commun , vol.22 , pp. 2219
- Malet, R.¹ Moreno-Manas, M.² Pleixats, R.³

25
- 37049083887
- (1995) J. Chem. Soc. Trans , vol.1 , pp. 1145
- Bennett, S.N.L.¹ Hall, R.G.²

26
- 84986379473
- (1992) Heteroatom Chem , vol.3 , pp. 563
- Imamoto, T.¹ Oshiki, T.² Onozawa, T.³ Matsuo, M.⁴ Hikosaka, T.⁵ Yanagawa, M.⁶

27
- 0034725879
- (2000) J. Org. Chem , vol.65 , pp. 4776
- Al-Masum, M.¹ Kumuraswamy, G.² Livinghouse, T.³

28
- 0000497218
- (1990) J. Org. Chem , vol.55 , pp. 5033
- Hinkle, R.J.¹ Stang, P.J.² Kowalski, M.H.³

29
- 0000005112
- (2000) Chem. Commun , pp. 1069
- Kwong, F.Y.¹ Chan, K.S.²

30
- 21144476906
- (1993) Phosphorus Sulfur Silicon , vol.79 , pp. 297
- Maffei, M.¹ Buono, G.²

31
- 0001582686
- (1998) Tetrahedron Lett , vol.30 , pp. 5393
- Holt, D.A.¹ Erb, J.M.²

32
- 0009296723
- For example
- (1962) J. Gen. Chem. USSR , vol.32 , pp. 3288
- Kabachnik, M.I.¹ Jung-yu, C.² Tsvetkob, E.N.³

33
- 84918067672
- (1960) Bull. Acad. Sci. USSR , vol.131 , pp. 1334
- Kabachnik, M.I.¹ Tsvetkov, E.N.² Jung-yu, C.³

34
- 0009218637
- (1981) J. Am. Chem. Soc , vol.103 , pp. 2292
- Loewus, D.I.¹

35
- 0009142789
- (1984) J. Gen. Chem. USSR , vol.54 , pp. 630
- Nifant'ev, E.E.¹ Magdeeva, R.K.² Solovetskaya, L.A.³ Sergeev, N.M.⁴

36
- 0001193974
- (1986) J. Gen. Chem. USSR , vol.56 , pp. 680
- Nifant'ev, E.E.¹ Solovetskaya, L.A.² Maslennikova, V.I.³ Magdeeva, R.K.⁴ Sergeev, N.M.⁵

37
- 0029098821
- (1995) J. Med. Chem , vol.38 , pp. 3297
- Froestl, W.¹ Mickel, S.J.² Hall, R.G.³ von Sprecher, G.⁴ Diel, P.J.⁵ Strub, D.⁶ Baumann, P.A.⁷ Brugger, F.⁸ Gentsch, C.⁹ Jaekel, J.¹⁰ Olpe, H.-R.¹¹ Rihs, G.¹² Vassout, A.¹³ Waldmeier, P.C.¹⁴ Bittiger, H.¹⁵

38
- 84949354260
- (1989) J. Phosphorus Sulfur Silicon , vol.45 , pp. 165
- Maier, L.¹ Diel, P.²

39
- 84992231546
- (1980) J. Gen. Chem. USSR , vol.50 , pp. 1026
- Platonov, A.Y.¹ Kruglov, A.S.² Chistoketov, V.N.³ Dogadina, A.V.⁴

40
- 84992242893
- We have previously introduced anilinium hypophosphite (1) as a convenient alternative to anhydrous hypophosphorous acid in several reactions (see [1]). This hypophosphite salt is crystalline (m.p. 113-114 C) and readily available inexpensively, and can be stored without particular precautions for several months, making it the ideal starting material for the preparation of organophosphorous compounds

41
- 33845378909
- Chem. Rev. , vol.85 , pp. 129
- Johnstone, R.A.W.¹ Wilby, A.H.²

42
- 0001667653
- (1985) J. Org. Chem , vol.50 , pp. 3408
- Boyer, S.K.¹ Bach, J.² McKenna, J.³ Jagdmann, E.⁴

43
- 0009211138
- Michael-like addition to alkenylphosphonous acids and related compounds has been reported previously
- (1962) J. Gen. Chem. USSR , vol.32 , pp. 3279
- Kabachnik, M.I.¹ Tsvetkov, E.N.² Zhun-yui, C.³

44
- 0002395359
- (1983) Phosphorous Sulfur , vol.17 , pp. 21
- Maier, L.¹ Rist, G.²

45
- 84992250578
- See also references [5b] and [6b]

46
- 0034692175
- (For an excellent review, see)
- (2000) J. Med. Chem , vol.43 , pp. 1427
- Chebib, M.¹ Johnston, G.A.R.²

47
- 0030567873
- (1996) Bioorg. Med. Chem. Lett , vol.6 , pp. 2073
- Murata, Y.¹ Woodward, R.M.² Miledi, R.³ Overman, L.E.⁴

48
- 0029859986
- (1996) Mol. Pharmacol , vol.50 , pp. 1024
- Ragozzino, D.¹ Woodward, R.M.² Murata, Y.³ Eusebi, F.⁴ Overman, L.E.⁵ Miledi, R.⁶

49
- 33749088627
- (1998) J. Chem. Soc. Perkin Trans , vol.1 , pp. 3241
- Kehler, J.¹ Ebert, B.² Dahl, O.³ Krogsgaard-Larsen, P.⁴

50
- 0035907483
- (2001) Bioorg. Med. Chem. Lett , vol.11 , pp. 1573
- Ebert, B.¹ Mortensen, M.² Thompson, S.A.³ Kehler, J.⁴ Wafford, K.A.⁵ Krogsgaard-Larsen, P.⁶

51
- 0033594164
- (1999) Bioorg. Med. Chem. Lett , vol.9 , pp. 811
- Kehler, J.¹ Stensbøl, B.² Krogsgaard-Larsen, P.³

52
- 0032544773
- (1998) Eur. J. Pharmacol , vol.357 , pp. 227
- Chebib, M.¹ Mewett, K.N.² Johnston, G.A.R.³

53
- 0026080085
- (1991) Synthesis , pp. 993
- Wustrow, D.J.¹ Wise, L.D.²

54
- 0000654946
- See example
- (1978) Russ. Chem. Rev , vol.47 , pp. 835
- Nifant'ev, E.E.¹

55
- 84953405629
- Wiley, New York
- (1996) The Chemistry of Organophosphorus Compounds , vol.4
- Hartley, F.R.¹

56
- 0004231121
- Wiley, New York
- (2000) Guide To Organophosphorus Chemistry
- Quin, L.D.A.¹

57
- 0033754701
- See also: and references cited therein
- (2000) Eur. J. Org. Chem , pp. 3497
- Soulier, E.¹ Yaouanc, J.-J.² Laurent, P.³ des Abbayes, H.⁴ Clément, J.-C.⁵

58
- 0032560134
- (1998) J. Med. Chem , vol.41 , pp. 1409
- Gangjee, A.¹ Elzein, E.² Queener, S.F.³ McGuire, J.J.⁴

59
- 84986525816
- (1988) J. Heterocyclic Chem , vol.25 , pp. 1237
- Martinez, A.G.¹ Herrera, A.² Martinez, R.³ Teso, E.⁴ Garcia, A.⁵ Osio, J.⁶ Pargada, L.⁷ Unanue, R.⁸ Subramanian, L.R.⁹ Hanack, M.¹⁰

60
- 0032986384
- (1999) Synth. Commun , vol.29 , pp. 409
- Lai, G.¹ McAllister, T.²

61
- 85007950754
- (1982) Synthesis , pp. 85
- Stang, P.J.¹ Hanack, M.² Subramanian, L.R.³

62
- 0016856645
- (1975) Am. Chem. Soc , vol.97 , pp. 857
- Sih, C.J.¹ Salomon, R.G.² Price, P.³ Sood, R.⁴ Peruzzotti, J.⁵

63
- 0000937935
- (1994) J. Org. Chem , vol.59 , pp. 3102
- Kropp, P.J.¹ Crawford, S.D.²

64
- 0003106727
- (1981) Tetrahedron Lett , vol.22 , pp. 85
- Sato, F.¹ Ishikawa, H.² Sato, M.³

65
- 0009290184
- (1982) J. Gen. Chem. USSR , vol.52 , pp. 2173
- Nifant'ev, E.E.¹ Magdeeva, R.K.² Maslennikova, V.I.³ Taber, A.M.⁴ Kalechits, I.V.⁵

66
- 0009223115
- (1986) J. Gen. Chem. USSR , vol.56 , pp. 1261
- Belakhov, V.V.¹ Yudelevich, V.I.² Fetter, A.P.³ Ionin, B.I.⁴

67
- 0000526513
- (1955) J. Am. Chem. Soc , vol.77 , pp. 929
- Walsh, E.N.¹ Beck, T.M.² Woodstock, W.H.³

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