Abstract
Novel main group element compounds, geminal dianionic derivatives of the heavier group 14 elements; namely, 1,1-dilithiosilanes, 1,1-dilithiogermanes and 1,1-dilithiostannanes (and closely related derivatives of the cyclopentadiene-1,1-diide and cyclobutadiene dianion), are the focus of the present review. The synthetic strategies for their preparation, structural features, and synthetic applications are discussed.
References
1.
10.1016/j.mencom.2015.05.001_bib0005
Grignard
Ann. Chim.,
1901
2.
Schlenk W., Holtz J.
Berichte der deutschen chemischen Gesellschaft,
1917
3.
Ziegler K., Nagel K., Patheiger M.
Zeitschrift fur Anorganische und Allgemeine Chemie,
1955
4.
Gurak J.A., Chinn J.W., Lagow R.J.
Journal of the American Chemical Society,
1982
5.
Kawa H., Manley B.C., Lagow R.J.
Journal of the American Chemical Society,
1985
6.
Chauhan H.P., Kawa H., Lagow R.J.
Journal of Organic Chemistry,
1986
7.
Kawa H., Manley B.C., Lagow R.J.
Polyhedron,
1988
8.
Baran J.R., Lagow R.J.
Journal of the American Chemical Society,
1990
9.
10.1016/j.mencom.2015.05.001_sbref0025b
Kawa
J. Chem. Soc., Chem. Commun.,1984,
1664
10.
Kaiser E.M., Hauser C.R.
Journal of the American Chemical Society,
1966
11.
Kaiser E.M., Solter L.E., Schwarz R.A., Beard R.D., Hauser C.R.
Journal of the American Chemical Society,
1971
12.
Kaiser E.M., Hauser C.R.
Tetrahedron Letters,
1967
13.
Gais H.J., Vollhardt J., Guenther H., Moskau D., Lindner H.J., Braun S.
Journal of the American Chemical Society,
1988
14.
Ong C.M., Stephan D.W.
Journal of the American Chemical Society,
1999
15.
Tamao K., Kawachi A.
Advances in Organometallic Chemistry,
1995
16.
Lickiss P.D., Smith C.M.
Coordination Chemistry Reviews,
1995
17.
Belzner J., Dehnert U.
Chemistry of Functional Groups,
1998
18.
Sekiguchi A., Lee V.Y., Nanjo M.
Coordination Chemistry Reviews,
2000
19.
P. Riviere, A. Castel and M. Riviere-Baudet, in The Chemistry of Organic Germanium, Tin and Lead Compounds, ed. Z. Rappoport, Wiley, Chichester, 2002, vol. 2. ch. 11.
20.
LERNER H.
Coordination Chemistry Reviews,
2005
21.
Saito M., Yoshioka M.
Coordination Chemistry Reviews,
2005
22.
V. Ya. Lee and A. Sekiguchi, in Reviews. of Reactive Intermediate Chemistry, eds. M. S. Platz, R.A. Moss and. M. Jones, Jr., Wiley-Interscience, Hoboken, 2007, ch. 2.
23.
Lee V.Y., Sekiguchi A.
Accounts of Chemical Research,
2007
24.
Scheschkewitz D.
Chemistry - A European Journal,
2009
25.
Lee V.Y., Sekiguchi A.
2010
26.
Rajca A., Wang P., Streitwieser A., Schleyer P.V.
Inorganic Chemistry,
1989
27.
Mehrotra S.K., Kawa H., Baran J.R., Ludvig M.M., Lagow R.J.
Journal of the American Chemical Society,
1990
28.
Tokitoh N., Hatano K., Sadahiro T., Okazaki R.
Chemistry Letters,
1999
29.
Sekiguchi A., Ichinohe M., Yamaguchi S.
Journal of the American Chemical Society,
1999
30.
Ichinohe M., Arai Y., Sekiguchi A., Takagi N., Nagase S.
Organometallics,
2001
31.
Igarashi M., Ichinohe M., Sekiguchi A.
Journal of the American Chemical Society,
2007
32.
Bravo-Zhivotovskii D., Ruderfer I., Melamed S., Botoshansky M., Tumanskii B., Apeloig Y.
Angewandte Chemie - International Edition,
2005
33.
Bravo-Zhivotovskii D., Ruderfer I., Melamed S., Botoshansky M., Schmidt A., Apeloig Y.
Angewandte Chemie - International Edition,
2006
34.
Bravo-Zhivotovskii D., Molev G., Kravchenko V., Botoshansky M., Schmidt A., Apeloig Y.
Organometallics,
2006
35.
Dobrovetsky R., Bravo-Zhivotovskii D., Tumanskii B., Botoshansky M., Apeloig Y.
Angewandte Chemie - International Edition,
2010
36.
Dobrovetsky R., Kratish Y., Tumanskii B., Botoshansky M., Bravo-Zhivotovskii D., Apeloig Y.
Angewandte Chemie - International Edition,
2012
37.
Bravo-Zhivotovskii D., Yuzefovich M., Sigal N., Korogodsky G., Klinkhammer K., Tumanskii B., Shames A., Apeloig Y.
Angewandte Chemie - International Edition,
2002
38.
Tokitoh N., Hatano K., Sasaki T., Sasamori T., Takeda N., Takagi N., Nagase S.
Organometallics,
2002
39.
Tajima T., Sasamori T., Takeda N., Tokitoh N., Yoshida K., Nakahara M.
Organometallics,
2005
40.
Sekiguchi A., Izumi R., Ihara S., Ichinohe M., Lee V.Y.
Angewandte Chemie - International Edition,
2002
41.
Lee V.Y., McNeice K., Ito Y., Sekiguchi A.
Chemical Communications,
2011
42.
Tajima T., Takeda N., Sasamori T., Tokitoh N.
European Journal of Inorganic Chemistry,
2005
43.
Tajima T., Ikeda M., Saito M., Ishimura K., Nagase S.
Chemical Communications,
2008
44.
Joo W., Hong J., Choi S., Son H., Hwan Kim C.
Journal of Organometallic Chemistry,
1990
45.
Hong J., Boudjouk P., Castellino S.
Organometallics,
1994
46.
West R., Sohn H., Bankwitz U., Calabrese J., Apeloig Y., Mueller T.
Journal of the American Chemical Society,
1995
47.
West R., Sohn H., Powell D.R., Müller T., Apeloig Y.
1996
48.
Saito M., Haga R., Yoshioka M., Ishimura K., Nagase S.
Angewandte Chemie - International Edition,
2005
49.
Saito M., Kuwabara T., Kambayashi C., Yoshioka M., Ishimura K., Nagase S.
Chemistry Letters,
2010
50.
Kuwabara T., Guo J., Nagase S., Minoura M., Herber R.H., Saito M.
Organometallics,
2014
51.
Saito M., Sakaguchi M., Tajima T., Ishimura K., Nagase S., Hada M.
Science,
2010
52.
Freeman W.P., Tilley T.D., Yap G.P., Rheingold A.L.
1996
53.
Freeman W.P., Tilley T.D., Liable-Sands L.M., Rheingold A.L.
Journal of the American Chemical Society,
1996
54.
Choi S., Boudjouk P., Wei P.
Journal of the American Chemical Society,
1998
55.
Liu Y., Stringfellow T.C., Ballweg D., Guzei I.A., West R.
Journal of the American Chemical Society,
2001
56.
Choi S., Boudjouk P., Hong J.
Organometallics,
1999
57.
58.
Choi S., Boudjouk P., Qin K.
Organometallics,
2000
59.
Liu Y., Ballweg D., Müller T., Guzei I.A., Clark R.W., West R.
Journal of the American Chemical Society,
2002
60.
Saito M., Shimosawa M., Yoshioka M., Ishimura K., Nagase S.
Organometallics,
2006
61.
Saito M., Shimosawa M., Yoshioka M., Ishimura K., Nagase S.
Chemistry Letters,
2006
62.
Lee V.Y., Takanashi K., Matsuno T., Ichinohe M., Sekiguchi A.
Journal of the American Chemical Society,
2004
63.
Lee V.Y., Takanashi K., Kato R., Matsuno T., Ichinohe M., Sekiguchi A.
Journal of Organometallic Chemistry,
2007
64.
Lee V.Y., Ito Y., Yasuda H., Takanashi K., Sekiguchi A.
Journal of the American Chemical Society,
2011
65.
Lee V.Y., Takanashi K., Ichinohe M., Sekiguchi A.
Angewandte Chemie - International Edition,
2004
66.
Takanashi K., Lee V.Y., Yokoyama T., Sekiguchi A.
Journal of the American Chemical Society,
2009
67.
Igarashi M., ıchinohe M., Sekiguchi A.
Heteroatom Chemistry,
2008
68.
Sekiguchi A., Izumi R., Lee V.Y., Ichinohe M.
Organometallics,
2003
69.
Lee V.Y., Kawai M., Sekiguchi A., Ranaivonjatovo H., Escudié J.
Organometallics,
2009
70.
Lee V.Y., Aoki S., Kawai M., Meguro T., Sekiguchi A.
Journal of the American Chemical Society,
2014
71.
Ichinohe M., Sanuki K., Inoue S., Sekiguchi A.
Organometallics,
2004
72.
Sekiguchi A., Izumi R., Lee V.Y., Ichinohe M.
Journal of the American Chemical Society,
2002
73.
Nakata N., Sekiguchi A.
Journal of the American Chemical Society,
2005
74.
Nakata N., Izumi R., Lee V.Y., Ichinohe M., Sekiguchi A.
Journal of the American Chemical Society,
2004
75.
Nakata N., Izumi R., Lee V.Y., Ichinohe M., Sekiguchi A.
Chemistry Letters,
2008
76.
Nakata N., Fujita T., Sekiguchi A.
Journal of the American Chemical Society,
2006
77.
Nakata N., Aoki S., Lee V.Y., Sekiguchi A.
Organometallics,
2015
78.
Ichinohe M., Igarashi M., Sanuki K., Sekiguchi A.
Journal of the American Chemical Society,
2005
79.
Lee V.Y., Yasuda H., Ichinohe M., Sekiguchi A.
Angewandte Chemie - International Edition,
2005
80.
Nakata N., Izumi R., Lee V.Y., Ichinohe M., Sekiguchi A.
Chemistry Letters,
2005
81.
The First Stable Heteracyclopropabenzene: Synthesis and Crystal Structure of a Silacyclopropabenzene
Hatano K., Tokitoh N., Takagi N., Nagase S.
Journal of the American Chemical Society,
2000
82.
Tajima T., Hatano K., Sasaki T., Sasamori T., Takeda N., Tokitoh N., Takagi N., Nagase S.
Journal of Organometallic Chemistry,
2003
83.
Tajima T., Hatano K., Sasaki T., Sasamori T., Takeda N., Tokitoh N.
Chemistry Letters,
2003
84.
Kuwabara T., Saito M., Guo J., Nagase S.
Inorganic Chemistry,
2013
85.
Kuwabara T., Guo J.D., Nagase S., Saito M.
Angewandte Chemie - International Edition,
2013
86.
Kuwabara T., Guo J., Nagase S., Sasamori T., Tokitoh N., Saito M.
Journal of the American Chemical Society,
2014
87.
Takanashi K., Lee V.Y., Matsuno T., Ichinohe M., Sekiguchi A.
Journal of the American Chemical Society,
2005
88.
Takanashi K., Lee V.Y., Ichinohe M., Sekiguchi A.
Angewandte Chemie - International Edition,
2006
89.
Takanashi K., Lee V.Y., Sekiguchi A.
Organometallics,
2009
90.
Takanashi K., Lee V.Y., Ichinohe M., Sekiguchi A.
European Journal of Inorganic Chemistry,
2007
91.
Lee V.Y., Takanashi K., Sekiguchi A.
Dalton Transactions,
2010
92.
Lee V.Y., Ito Y., Sekiguchi A.
Russian Chemical Bulletin,
2013
93.
Lee V.Y., Aoki S., Yokoyama T., Horiguchi S., Sekiguchi A., Gornitzka H., Guo J., Nagase S.
Journal of the American Chemical Society,
2013
94.
Lee V.Y., Takanashi K., Matsuno T., Ichinohe M., Sekiguchi A.
Applied Organometallic Chemistry,
2010
95.
Lee V., Yokoyama T., Takanashi K., Sekiguchi A.
Chemistry - A European Journal,
2009
96.
Takanashi K., Lee V.Y., Ichinohe M., Sekiguchi A.
Chemistry Letters,
2007
97.
Lee V.Y., Ito Y., Sekiguchi A., Gornitzka H., Gapurenko O.A., Minkin V.I., Minyaev R.M.
Journal of the American Chemical Society,
2013
98.
Lee V.Y., Ito Y., Gapurenko O.A., Sekiguchi A., Minkin V.I., Minyaev R.M., Gornitzka H.
Angewandte Chemie - International Edition,
2015