Communication
ChemComm
G. P. Rosini, K. Krogh-Jespersen, A. S. Goldman, M. Gupta, 10 The solvent(s) used to grow crystals: toluene–pentane for 1a,
C. M. Jensen and W. C. Kaska, Chem. Commun., 1997, 2273–2274;
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toluene–pentane for 1b, and benzene for 1c. All solvents were dried
by standard methods prior to use.
Chem. Soc., 1999, 121, 4086–4087; (d) M. W. Haenel, S. Oevers, 11 Also see: S. Biswas, Z. Huang, Y. Choliy, D. Y. Wang, M. Brookhart,
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13276–13295.
K. Krogh-Jespersen and A. S. Goldman, J. Am. Chem. Soc., 2004, 126, 12 (a) Boronic Acids: Preparation and Applications in Organic Synthesis and
13044–13053; ( f ) A. S. Goldman, A. H. Roy, Z. Huang, R. Ahuja,
W. Schinski and M. Brookhart, Science, 2006, 312, 257–261;
(g) R. Ahuja, B. Punji, M. Findlater, C. Supplee, W. Schinski, 13 M. Vilches-Herrera, L. Domke and A. Borner, ACS Catal., 2014, 4,
M. Brookhart and A. S. Goldman, Nat. Chem., 2011, 3, 167–171; 1706–1724, and references therein.
(h) J. J. Adams, N. Arulsamy and D. M. Roddick, Organometallics, 14 L. Zhang, D. Peng, X. Leng and Z. Huang, Angew. Chem., Int. Ed.,
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5 Related (PCP)Ir complexes: (a) S. A. Kuklin, A. M. Sheloumov, 15 Control experiments with 1b and NaBHEt3, but with no hydrobora-
Medicine, ed. D. G. Hall, Wiley-VCH, Weinheim, 2005; (b) C. M. Crudden
and D. Edwards, Eur. J. Org. Chem., 2003, 4695–4712.
¨
F. M. Dolgushin, M. G. Ezernitskaya, A. S. Peregudov,
P. V. Petrovskii and A. A. Koridze, Organometallics, 2006, 25,
5466–5476; (b) Y. Shi, T. Suguri, C. Dohi, H. Yamada, S. Kojima
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tion catalyst 3; and 3 and NaBHEt3, but with no isomerization
catalyst 1b, were conducted. In neither case was any linear hydro-
boration product 5 detected. In the reaction with 1b and NaBHEt3,
but with no 3, a trace amount (o5%) of branched octylboronate
esters were detected by GC and GC/MS.
¨
6 I. Gottker-Schnetmann, P. White and M. Brookhart, J. Am. Chem.
Soc., 2004, 126, 1804–1811.
16 It should be noted that Crudden and Srebnic have reported the
selective conversion of internal olefins into linear boronates cata-
lyzed by a Rh catalyst. However, the scope of the reactions was
limited to non-functionalized monoenes. See: (a) D. R. Edwards,
C. M. Crudden and K. Yam, Adv. Synth. Catal., 2005, 347, 50–54;
(b) S. Pereira and M. Srebnik, J. Am. Chem. Soc., 1996, 118, 909–910.
7 Very recently, a highly active (PSCOP)Ir catalyst has been reported
for transfer alkane dehydrogenation. W. Yao, Y. Zhang, X. Jia and
Z. Huang, Angew. Chem., Int. Ed., 2014, 53, 1390–1394.
8 (a) W. Zuo and P. Braunstein, Organometallics, 2012, 31, 2606–2615;
(b) A. R. Chianese, S. E. Shaner, J. A. Tendler, D. M. Pudalov,
D. Y. Shopov, D. Kim, S. L. Rogers and A. Mo, Organometallics, 17 During the review of this manuscript, Obligacion and Chirik
2012, 31, 7359–7367; (c) K. E. Allen, M. D. Heinekey, A. S. Goldman
and K. I. Goldberg, Organometallics, 2013, 32, 1579–1582.
9 J. C. Grimm, C. Nachtigal, H. G. Mack, W. C. Kaska and H. A. Mayer,
Inorg. Chem. Commun., 2000, 3, 511–514.
reported a cobalt-catalyzed tandem olefin isomerization–hydrobora-
tion. The system can tolerate ester functionalities. See:
J. V. Obligacion and P. J. Chirik, J. Am. Chem. Soc., 2013, 135,
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