Abstract
For several decades, the concerted or stepwise character of the mechanism of the 1,3-dipolar cycloaddition reaction has been one of the most debated issues in the field of organic chemistry. The significance of this problem is due to the fact that in a catalyst-free 1,3-dipolar cycloaddition, when the mechanism switches from concerted to stepwise, the stereospecificity is lost and thus unwanted stereoisomers may emerge. The first proposals about the mechanism of the 1,3-dipolar reaction were due to Huisgen (concerted model) and subsequently by Firestone (two-step diradical channel) in the 1960s. After a decade of debate, most researchers accepted the concerted model for the reaction, but during these years, researchers reported some examples of the stepwise mechanism for catalyst-free 1,3-dipolar cycloadditions. This review attempts to find a number of factors that could influence the reaction channels and switch the mechanism from concerted to stepwise, or vice versa.
Keywords
References
1.
Lan
Y.
, and
Houk
K.N.
(2010 ) J. Am. Chem.
Soc. , 132 , 17921 .
2.
Freindorf
M.
,
Sexton
T.
,
Kraka
E.
, and
Cremer
D.
(2014 ) Theor. Chem.
Acc. , 133 , 1 .
3.
Okazaki
R.
,
Ishii
N.
, and
Inamoto
A.
(1987 ) J. Am. Chem.
Soc. , 109 , 279 .
4.
Khlebnikov
A.F.
,
Konev
A.S.
,
Virtsev
A.A.
2014 ) Helv. Chim. Acta , 97 ,
453 .
5.
Rossum
T.
,
Kengen
S.W.
, and
Oost
J.
(2013 ) FEBS J. ,
280 , 2979 .
6.
Bhushan
R.
, and
Dubey
R.
(2012 ) Biomed.
Chromatogr. , 26 , 471 .
7.
Chen
W.
,
Du
W.
,
Duan
Y.Z.
2007 ) Angew. Chem. , 119 ,
7811 .
8.
Patel
R.N.
(2001 ) Curr. Opin. Chem.
Biol. , 12 , 587 .
9.
Coleman
W.M.
,
Perfetti
T.A.
, and
Lawrence
B.M.
(1998 ) J. Chromatogr.
Sci. , 36 , 575 .
10.
Maier
N.M.
,
Franco
P.
, and
Lindner
W.
(2001 ) J. Chromatography
A , 906 , 3 .
11.
Chankvetadze
B.
(2012 ) J. Chromatography
A , 1269 , 26 .
12.
Huisgen
R.
(1963 ) Angew. Chem., Int. Ed.
Engl. , 2 , 565 .
13.
Firestone
R.A.
(1968 ) J. Org.
Chem. , 33 , 2285 .
14.
Houk
K.N.
,
Sims
J.
,
Watts
C.R.
, and
Luskus
L.J.
(1973 ) J. Am. Chem.
Soc. , 95 , 7301 .
15.
Motion
K.R.
,
Robertson
I.R.
,
Sharp
J.T.
, and
Walkinshaw
M.D.
(1992 ) J. Chem. Soc., Perkin
Trans. 1 , 13 , 1709 .
16.
Di Valentin
C.
,
Freccero
M.
,
Gandolfi
R.
, and
Rastelli
A.
(2000 ) J. Org. Chem. ,
65 , 6112 .
17.
Curtius
T.
(1883 ) Ber. Dtsch. Chem.
Ges. , 16 , 2230 .
18.
Buchner
E.
(1888 ) Ber. Dtsch. Chem.
Ges. , 21 , 2637 .
19.
Michael
A.
(1893 ) J. Prakt.
Chem. , 48 , 94 .
20.
Pechmann
H.V.
(1894 ) Ber. Dtsch. Chem.
Ges. , 27 , 1888 .
21.
Beckmann
E.
(1890 ) Ber. Dtsch. Chem.
Ges. , 23 , 3331 .
22.
Werner
A.
, and
Buss
H.
(1894 ) Ber. Dtsch. Chem.
Ges. , 27 , 2193 .
23.
Jensen
K.B.
,
Gothelf
K.V.
,
Hazell
R.G.
, and
Jorgensen
K.A.
(1997 ) J. Org.
Chem. , 62 , 2471 .
24.
Hoogenboom
J.
,
Zuilhof
H.
, and
Wennekes
T.
(2015 ) Org. Lett. ,
17 , 5550 .
25.
Smith
L.I.
(1938 ) Chem. Rev. ,
23 , 193 .
26.
John
P.R.
(2010 ) Synthesis and
transformations of a few nitrogen and oxygen heterocycles ,
Cochin University of Science and
Technology .
27.
Cox
A.
,
Thomas
L.
, and
Sheridan
J.
(1958 ) Nature ,
181 , 1000 .
28.
Muller
E.
, and
Rundel
W.
(1956 ) Chem. Ber. ,
89 , 1065 .
29.
Huisgen
R.
,
Scheer
W.
, and
Huber
H.
(1967 ) J. Am. Chem.
Soc. , 89 , 1753 .
30.
Huisgen
R.
,
Grashey
R.
, and
Sauer
J.
(1964 ) The Alkenes ,
1 , 739 .
31.
Woodward
R.B.
, and
Hoffmann
R.
(1969 ) Angew. Chem. Int.
Ed. , 8 , 781 .
32.
Fukui
K.
,
Yonezawa
T.
,
Nagata
C.
, and
Shingu
H.
(1954 ) J. Chem.
Phys. , 22 , 1433 .
33.
Harris
F.E.
(1967 ) Adv. Quantum
Chem. , 3 , 61 .
34.
Firestone
R.A.
(1970 ) J. Chem. Soc.,
A , 92 , 1570 .
35.
Firestone
R.A.
(1972 ) J. Org.
Chem. , 37 , 2181 .
36.
Firestone
R.A.
(1977 ) Tetrahedron ,
33 , 3009 .
37.
Huisgen
R.
(1976 ) J. Org. Chem. ,
41 , 403 .
38.
Houk
K.N.
,
Firestone
R.A.
,
Munchausen
L.L.
1985 ) J. Am. Chem. Soc. , 107 ,
7227 .
39.
Huisgen
R.
, and
Weinberger
R.
(1985 ) Tetrahedron
Lett. , 26 , 5119 .
40.
Tsuge
O.
,
Kanemasa
S.
, and
Takenaka
S.
(1985 ) Bull. Chem. Soc.
Jpn , 58 , 3137 .
41.
Dignam
K.J.
,
Hegarty
A.F.
, and
Quain
P.L.
(1978 ) J. Org.
Chem. , 43 , 388 .
42.
Huisgen
R.
,
Mlostoń
G.
, and
Langhals
E.
(1986 ) J. Org. Chem. ,
51 , 4085 .
43.
Huisgen
R.
,
Mlostoń
G.
, and
Langhals
E.
(1986 ) J. Am. Chem.
Soc. , 108 , 6401 .
44.
Quast
H.
,
Regnat
D.
,
Peters
E.M.
1994 ) Chem. Ber. , 127 ,
2527 .
45.
Padwa
A.
, and
Pearson
W.H.
(2003 ) Synthetic
applications of 1, 3-dipolar cycloaddition chemistry toward heterocycles and natural
products.
John Wiley and Sons , New York,
USA
46.
Huisgen
R.
,
Mlostoń
G.
,
Giera
H.
, and
Langhals
E.
(2002 ) Tetrahedron ,
58 , 507 .
47.
Bohm
A.
,
Webber
A.
, and
Sauer
J.
(1999 ) Tetrahedron ,
55 , 9535 .
48.
Domingo
L.R.
, and
Picher
M.F.
(2004 ) Tetrahedron ,
60 , 5053 .
49.
Kuznetsov
M.L.
(2006 ) Russ. Chem.
Rev. , 75 , 935 .
50.
Firestone
R.A.
(2013 ) Int. J. Chem.
Kinet. , 45 , 415 .
51.
Jasiński
R.
(2013 ) Tetrahedron ,
69 , 927 .
52.
Mlostoń
G.
,
Pipiak
P.
,
Linden
A.
, and
Heimgartner
H.
(2015 ) Helv. Chim.
Acta , 98 , 462 .
53.
Mlostoń
G.
,
Urbaniak
K.
,
Linden
A.
, and
Heimgartner
H.
(2015 ) Helv. Chim.
Acta , 98 , 453 .
54.
Siadati
S.A.
(2015 ) Tetrahedron
Lett. , 56 , 4857 .
55.
Siadati
S.A.
(2016 ) Comb. Chem. High.
Throughput Screen , 19 , 170 .
56.
Quast
H.
,
Regnat
D.
,
Peters
E.M.
1990 ) Angew. Chem. Int. Ed. , 29 ,
695 .
57.
Pandey
G.
,
Banerjee
P.
, and
Gadre
S.R.
(2006 ) Chem. Rev. ,
106 , 4484 .
58.
Coldham
I.
, and
Hufton
R.
(2005 ) Chem. Rev. ,
105 , 2765 .
59.
Jasiński
R.
(2015 ) Monatsh.
Chem. , 146 , 591 .
60.
Jasiński
R.
,
Kwiatkowska
M.
, and
Barański
A.
(2007 ) Wiad. Chem. ,
61 , 485 .
61.
Mlostoń
G.
,
Urbaniak
K.
,
Gębicki
K.
2014 ) Heteroatom Chem. , 25 ,
548 .
62.
Siadati
S.A.
(2016 ) Helv. Chim.
Acta , doi: 10.1002/hlca.201500165.
63.
Yang
X.
, and
Xue
Y.
(2014 ) J. Org Chem. ,
79 , 4863 .
64.
Jasiński
R.
(2015 ) Tetrahedron
Lett. , 56 , 532 .
65.
Siadati
S.A.
(2015 ) J. Chem.
Res. , 39 , 640 .
66.
Baran
J.
, and
Mayr
H.
(1987 ) J. Am. Chem.
Soc. , 109 , 6519 .
67.
Baran
J.
, and
Mayr
H.
(1989 ) J. Org. Chem. ,
54 , 5774 .
68.
Harkness
J.M.
,
Kistiakowski
G.B.
, and
Mears
W.H.
(1937 ) J. Chem.
Phys. , 5 , 682 .
69.
Huisgen
R.
,
Penelle
J.
,
Mlostoń
G.
1992 ) J. Am. Chem. Soc. , 114 ,
266 .
70.
Jasiński
R.
(2015 ) RSC Adv. ,
5 , 101045 .
71.
Henke
B.R.
,
Kouklis
A.J.
, and
Heathcock
C.H.
(1992 ) J. Org.
Chem. , 57 , 7056 .
72.
Asveld
E.W.H.
, and
Kellogg
R.M.
(1980 ) J. Am. Chem.
Soc. , 102 , 3644 .
73.
Hitzler
M.G.
,
Freyhardt
C.C.
, and
Jochims
J.C.
(1996 ) J. Prakt.
Chem. , 338 , 243 .
74.
Gerbaux
P.
,
Barbieux-Flammang
M.
,
Flammang
F.
, and
Bouchoux
G.
(2002 ) Int. J. Mass
Spectrom. , 219 , 643 .
75.
de Vivie-Riedle
R.
, and
Trauner
D.
Photochemical synthesis of intricarene
http://www.internetchemie.info/news/2014/dec14/intricaren-synthese.php
[accessed 24 August 2016].
76.
de Vivie-Riedle
R.
, and
Trauner
D.
(2014 ) Photochemical synthesis
of intricarene.
http://www.internetchemie.info/news/2014/dec14/intricarene-syntheses.php
[accessed 10 August 2016].
77.
Tanaka
J.
, and
Kanemasa
S.
(2001 ) Tetrahedron ,
57 , 899 .
78.
Gothelf
K.V.
,
Thomsen
I.
, and
Jorgensen
K.A.
(1996 ) J. Am. Chem.
Soc. , 118 , 59 .
79.
Šnieżek
M.
,
Stecko
S.
,
Panfil
I.
2013 ) Tetrahedron: Asymmetry , 24 ,
89 .
80.
Novikov
A.S.
, and
Kuznetsov
M.L.
(2012 ) Inorg. Chim.
Acta , 380 , 78 .
81.
Vivanco
S.
,
Lecea
B.
,
Arrieta
A.
2000 ) J. Am. Chem. Soc. , 122 ,
6078 .
82.
Huisgen
R.
,
Li
X.
,
Mlostoń
G.
, and
Fulka
C.
(2000 ) Eur. J. Org. Chem.,
9 , 1695 .
83.
Horn
B.A.
,
Herek
J.L.
, and
Zewail
A.H.
(1996 ) J. Am. Chem.
Soc. , 118 , 8755 .