Organic Letters
Letter
Compounds, Part 2; Rappoport, Z., Apeloig, Y., Eds.; Wiley:
Chichester, U.K., 1998; pp 595−701.
AUTHOR INFORMATION
Corresponding Author
■
(7) Corey, J. Y. J. Am. Chem. Soc. 1975, 97, 3237−3238.
(8) Cyclopropane formation starting from γ-haloalkyl silicon
precursors was described by Sommer and co-workers: (a) Sommer,
L. H.; Strien, R. E. V.; Whitmore, F. C. J. Am. Chem. Soc. 1949, 71,
3056−3060. For additional solvolysis experiments, see also:
(b) Shiner, V. J., Jr.; Ensinger, M. W.; Rutkowske, R. D. J. Am.
Chem. Soc. 1987, 109, 804−809. (c) Davidson, E. R.; Shiner, V. J. J.
Am. Chem. Soc. 1986, 108, 3135−3137. (d) Nakashima, T.; Fujiyama,
R.; Fujio, M.; Tsuno, Y. Tetrahedron Lett. 1999, 40, 539−542. For a
recent review, see: (e) Creary, X. Beilstein J. Org. Chem. 2019, 15,
1769−1780.
̈
Martin Oestreich − Technische Universitat Berlin, Berlin,
Other Authors
̈
Avijit Roy − Technische Universitat Berlin, Berlin,
Vittorio Bonetti − Technische Universitat Berlin, Berlin,
Guoqiang Wang − Technische Universitat Berlin, Berlin,
Qian Wu − Technische Universitat Berlin, Berlin,
(9) For an evaluation of β- and γ-silicon effects, see: Sugawara, M.;
Yoshida, J.-i. J. Org. Chem. 2000, 65, 3135−3142.
(10) (a) Davidson, E. R.; Shiner, V. J., Jr. J. Am. Chem. Soc. 1986,
108, 3135−3137. (b) Ref 8b.
(11) Nagahara, S.; Yamakawa, T.; Yamamoto, H. Tetrahedron Lett.
2001, 42, 5057−5060.
Hendrik F. T. Klare − Technische Universitat Berlin,
(12) Wang, D.; Xue, X.-S.; Houk, K. N.; Shi, Z. Angew. Chem., Int.
Ed. 2018, 57, 16861−16865.
(13) (a) Zhang, Z.-Y.; Liu, Z.-Y.; Guo, R.-T.; Zhao, Y.-Q.; Li, X.;
Wang, X.-C. Angew. Chem., Int. Ed. 2017, 56, 4028−4032. (b) Morton,
J. G. M.; Dureen, M. A.; Stephan, D. W. Chem. Commun. 2010, 46,
8947−8949.
Complete contact information is available at:
Notes
(14) For an iridium-catalyzed ring-opening hydrosilylation of
unactivated cyclopropanes with the aid of a directing group, see:
Murai, M.; Nishiyama, A.; Nishinaka, N.; Morita, H.; Takai, K. Chem.
Commun. 2017, 53, 9281−9284.
(15) Cyclopropanes are known to ring open upon being treated with
tetrachlorodiborane to afford 1,3-diborylated products: (a) Ceron, P.;
Finch, A.; Frey, J.; Kerrigan, J.; Parsons, T.; Urry, G.; Schlesinger, H.
I. J. Am. Chem. Soc. 1959, 81, 6368−6371. (b) Zeldin, M.; Rosen, A. J.
Organomet. Chem. 1972, 34, 259−268.
(16) Wu, Q.; Roy, A.; Irran, E.; Qu, Z.-W.; Grimme, S.; Klare, H. F.
T.; Oestreich, M. Angew. Chem., Int. Ed. 2019, 58, 17307−17311.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
A.R. gratefully acknowledges the Berlin Graduate School of
Natural Sciences and Engineering for a predoctoral fellowship
(2018−2021). G.W. and Q.W. thank the China Scholarship
Council (2019−2020) and the Alexander von Humboldt
Foundation (2017−2019), respectively, for postdoctoral
fellowships. The work was also funded by the Deutsche
Forschungsgemeinschaft (DFG, German Research Founda-
tion) under Germany’s Excellence Strategy (EXC 2008/1-
390540038). All theoretical calculations were performed at the
High-Performance Computing Center (HPCC) of Nanjing
University. M.O. is indebted to the Einstein Foundation Berlin
for an endowed professorship.
̈
̈
(17) (a) Schafer, A.; Reißmann, M.; Jung, S.; Schafer, A.; Saak, W.;
̈
Brendler, E.; Muller, T. Organometallics 2013, 32, 4713−4722.
(b) Omann, L.; Pudasaini, B.; Irran, E.; Klare, H. F. T.; Baik, M.-H.;
Oestreich, M. Chem. Sci. 2018, 9, 5600−5607.
(18) (a) Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215−
241. (b) Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157−167.
(19) Connelly, S. J.; Kaminsky, W.; Heinekey, D. M. Organometallics
2013, 32, 7478−7481.
(20) For selected reviews of transition-metal-catalyzed C−C bond
cleavage in strained ring systems, see: (a) Fumagalli, G.; Stanton, S.;
Bower, J. F. Chem. Rev. 2017, 117, 9404−9432. (b) Rubin, M.;
Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117−3179.
REFERENCES
■
(1) (a) Walker, J. C. L.; Klare, H. F. T.; Oestreich, M. Nat. Rev.
Chem. 2020, 4, 54−62. (b) Schulz, A.; Villinger, A. Angew. Chem., Int.
Ed. 2012, 51, 4526−4528. (c) Klare, H. F. T.; Oestreich, M. Dalton
Trans 2010, 39, 9176−9184.
(2) For general reviews, see: (a) Lee, V. Ya. Russ. Chem. Rev. 2019,
88, 351−369. (b) Lee, V. Ya.; Sekiguchi, A. In Organosilicon
Compounds; Lee, V. Ya., Ed.; Academic Press: Oxford, U.K., 2017;
Vol. 1, pp 197−230. (c) Muller, T. In Functional molecular silicon
̈
compounds I; Scheschkewitz, D., Ed.; Springer: Cham, Switzerland,
2014; pp 107−162.
(3) Reed, C. A. Acc. Chem. Res. 1998, 31, 325−332.
(4) C = X hydrosilylation: (a) Lambert, J. B.; Zhao, Y.; Wu, H. J.
Org. Chem. 1999, 64, 2729−2736. (b) Mu
̈
ther, K.; Oestreich, M.
ther, K.; Mohr, J.;
Chem. Commun. 2011, 47, 334−336. (c) Mu
̈
Oestreich, M. Organometallics 2013, 32, 6643−6646.
(5) C−F bond activation: (a) Klare, H. F. T. ACS Catal. 2017, 7,
6999−7002 (perspective). (b) Scott, V. J.; Çelenligil-Çetin, R.;
Ozerov, O. V. J. Am. Chem. Soc. 2005, 127, 2852−2853. (c) Panisch,
R.; Bolte, M.; Muller, T. J. Am. Chem. Soc. 2006, 128, 9676−9682.
̈
(d) Allemann, O.; Duttwyler, S.; Romanato, P.; Baldridge, K. K.;
Siegel, J. S. Science 2011, 332, 574−577. (e) Shao, B.; Bagdasarian, A.
L.; Popov, S.; Nelson, H. M. Science 2017, 355, 1403−1407.
(6) (a) Lambert, J. B.; Zhao, Y.; Emblidge, R. W.; Salvador, L. A.;
Liu, X.; So, J.-H.; Chelius, E. C. Acc. Chem. Res. 1999, 32, 183−190.
(b) Siehl, H.-U.; Muller, T. In The Chemistry of Organic Silicon
̈
D
Org. Lett. XXXX, XXX, XXX−XXX