ACS Catalysis
Letter
1
999, 1790−1792. (c) Kim, S.; Takeuchi, D.; Osakada, K. J. Am. Chem.
270−275. (d) Itazaki, M.; Nishihara, Y.; Takimoto, H.; Yoda, M.;
Osakada, K. J. Mol. Catal. A: Chem. 2005, 241, 65−71. (e) Shi, M.;
Wang, B.-Y.; Huang, J.-W. J. Org. Chem. 2005, 70, 5606−5610.
(f) Shao, L.-X.; Li, J.; Wang, B.-Y.; Shi, M. Eur. J. Org. Chem. 2010,
6448−6453. See also refs 5b and 5g.
(13) Oxidative addition of Si−B bond to Pt(0), see: (a) Sagawa, T.;
Asano, Y.; Ozawa, F. Organometallics 2002, 21, 5879−5886.
(b) Durieux, G.; Gerdin, M.; Moberg, C.; Jutand, A. Eur. J. Inorg.
Chem. 2008, 4236−4241.
(14) For insertion of C−C triple bond into the Pt−B bond, see ref
13a.
(15) The pathway involving oxidative addition of the proximal C−C
bond of MCP has been proposed in refs 2g, 8a, and 12a.
(16) One of the possible undesired pathways via G′ is the pathway
involving cleavage of the distal C−C bond to form π-allylplatinum. See
refs 4d, 4e, and 12c.
Soc. 2002, 124, 762−763. (d) Kim, S.; Takeuchi, D.; Osakada, K.
Macromol. Chem. Phys. 2003, 204, 666−673. (e) Taniguchi, H.;
Ohmura, T.; Suginome, M. J. Am. Chem. Soc. 2009, 131, 11298−
1
4
1299. (f) Ogata, K.; Atsuumi, Y.; Fukuzawa, S. Org. Lett. 2010, 12,
536−4539. (g) Terao, J.; Tomita, M.; Prakash, S.; Kambe, N. Angew.
Chem., Int. Ed. 2010, 49, 144−147. (h) Ogata, K.; Shimada, D.;
Furuya, S.; Fukuzawa, S. Org. Lett. 2013, 15, 1182−1185.
(
3) Examples for formation of B through cleavage of bond b:
(
5
a) Smolensky, E.; Kapon, M.; Eisen, M. S. Organometallics 2005, 24,
495−5498. (b) Smolensky, E.; Kapon, M.; Eisen, M. S. Organo-
metallics 2007, 26, 4510−4527. (c) Inami, T.; Sako, S.; Kurahashi, T.;
Matsubara, S. Org. Lett. 2011, 13, 3837−3839. (d) Inami, T.;
Kurahashi, T.; Matsubara, S. Chem. Commun. 2011, 47, 9711−9713
See also ref 2g. .
(
4) Examples for formation of C or D through cleavage of bond c:
a) Bapuji, S. A.; Motherwell, W. B.; Shipman, M. Tetrahedron Lett.
989, 30, 7107−7110. (b) Lautens, M.; Ren, Y.; Delanghe, P. H. M. J.
(
1
(17) The steric effect of the silyl group on isomer selectivity has been
discussed in the study on silaboration of 1-alkene. Suginome, M.;
Nakamura, H.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 2516−
Am. Chem. Soc. 1994, 116, 8821−8822. (c) Lautens, M.; Ren, Y. J. Am.
Chem. Soc. 1996, 118, 9597−9605. (d) Tsukada, N.; Shibuya, A.;
Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123−8124.
2
518.
(
6
e) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63,
458−6459.
5) (a) Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002,
3, 2059−2061. (b) Itazaki, M.; Nishihara, Y.; Osakada, K. J. Org.
(
4
Chem. 2002, 67, 6889−6895. (c) Takeuchi, D.; Osakada, K. Chem.
Commun. 2002, 646−647. (d) Takeuchi, D.; Anada, K.; Osakada, K.
Macromolecules 2002, 35, 9628−9633. (e) Takeuchi, D.; Anada, K.;
Osakada, K. Angew. Chem., Int. Ed. 2004, 43, 1233−1235.
(
f) Kozhushkov, S. I.; Yufit, D. S.; Ackermann, L. Org. Lett. 2008,
1
2
0, 3409−3412. (g) Shirakura, M.; Suginome, M. J. Am. Chem. Soc.
009, 131, 5060−5061. (h) Ackermann, L.; Kozhushkov, S. I.; Yufit,
D. S. Chem. - Eur. J. 2012, 18, 12068−12077. (i) Schinkel, M.;
Wallbaum, J.; Kozhushkov, S. I.; Marek, I.; Ackermann, L. Org. Lett.
2
013, 15, 4482−4484. (j) Sakae, R.; Matsuda, N.; Hirano, K.; Satoh,
T.; Miura, M. Org. Lett. 2014, 16, 1228−1231.
6) Kitatani, K.; Hiyama, T.; Nozaki, H. Bull. Chem. Soc. Jpn. 1977,
0, 3288−3294.
7) (a) Beletskaya, I.; Moberg, C. Chem. Rev. 2006, 106, 2320−2354.
(
5
(
(
(
(
b) Burks, H. E.; Morken, J. P. Chem. Commun. 2007, 4717−4725.
c) Ohmura, T.; Suginome, M. Bull. Chem. Soc. Jpn. 2009, 82, 29−49.
d) Suginome, M.; Ohmura, T. In Boronic Acids, 2nd ed.; Hall, D., Ed.;
Wiley-VCH: New York, 2011; Vol. 1, pp 171−212. (e) Oestreich, M.;
Hartmann, E.; Mewald, M. Chem. Rev. 2013, 133, 402−441.
(
8) (a) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000,
1
22, 11015−11016. (b) Pohlmann, T.; de Meijere, A. Org. Lett. 2000,
2
, 3877−3879. (c) Ohmura, T.; Taniguchi, H.; Kondo, Y.; Suginome,
M. J. Am. Chem. Soc. 2007, 129, 3518−3519. (d) Ohmura, T.;
Taniguchi, H.; Suginome, M. Org. Lett. 2009, 11, 2880−2883.
(
e) Akai, Y.; Yamamoto, T.; Nagata, Y.; Ohmura, T.; Suginome, M.
J. Am. Chem. Soc. 2012, 134, 11092−11095.
(
9) Silylboronic ester 6 was prepared by the reaction of i-PrPh SiLi
2
with i-PrOB(pin) (2 equiv) according to the reported procedure.
Suginome, M.; Matsuda, T.; Ito, Y. Organometallics 2000, 19, 4647−
4649.
(
3
(
1
10) Lewis, L. N.; Krafft, T. A.; Huffman, J. C. Inorg. Chem. 1992, 31,
555−3557.
11) Typical procedure is given for the reaction of 1b with 6 (entry
). Pt (dba) (1.1 mg, 1.0 mmol), 6 (35 mg, 0.10 mmol) and 1b (32
2
3
mg, 0.20 mmol) were dissolved in 100 mL of toluene in a screw-
capped vial and the mixture was stirred at 28 °C for 4 h. The reaction
was monitored by GC. After removal of the volatile materials, the
reaction mixture was purified by silica gel chromatography
(
hexane:Et O = 19:1) to give 7b (47 mg, 92%).
2
(
12) For transition-metal-catalyzed isomerization of MCPs to 1,3-
dienes, see: (a) Osakada, K.; Takimoto, H.; Yamamoto, T.
Organometallics 1998, 17, 4532−4534. (b) Nishihara, Y.; Yoda, C.;
Osakada, K. Organometallics 2001, 20, 2124−2126. (c) Camacho, D.
H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66,
3
077
ACS Catal. 2015, 5, 3074−3077