Chemical Science
Edge Article
chemistry.39 Further developments and applications in catalysis
are underway and will be reported in due course.
(c) Y. Wang and V. Gevorgyan, Angew. Chem., Int. Ed., 2015,
54, 2255–2259.
8 2-Pyridyl: (a) J.-H. Chu, P.-S. Lin and M.-J. Wu,
Organometallics, 2010, 29, 4058–4065. For recent examples
of the use of this group in C–H functionalization, see: (b)
M. Kim, S. Sharma, J. Park, M. Kim, Y. Choi, Y. Jeon,
J. H. Kwak and I. S. Kim, Tetrahedron, 2013, 69, 6552–6559;
(c) B. Liu, H.-Z. Jiang and B.-F. Shi, J. Org. Chem., 2014, 79,
1521–1526; (d) W. Zhang, J. Zhang, S. Ren and Y. Liu, J.
Org. Chem., 2014, 79, 11508–11516.
Acknowledgements
The University of Georgia is acknowledged for support of this
research. The Summer Undergraduate Research Opportunity
program at UGA is acknowledged for support of JOR.
9 2-Pyridinylmethyl: X. Cong, J. You, G. Gao and J. Lan, Chem.
Commun., 2013, 49, 662–664.
Notes and references
1 (a) K. Godula and D. Sames, Science, 2006, 312, 67–72; (b) 10 Pivaloyl: B. Xiao, Y. Fu, J. Xu, T.-J. Gong, J.-J. Dai, J. Yi and
X. Chen, K. M. Engle, D.-H. Wang and J.-Q. Yu, Angew. L. Liu, J. Am. Chem. Soc., 2010, 132, 468–469.
Chem., Int. Ed., 2009, 48, 5094–5115; (c) L. McMurray, 11 2-Carboxypropan-2-yl: H.-X. Dai, G. Li, X.-G. Zhang,
F. O'Hara and M. J. Gaunt, Chem. Soc. Rev., 2011, 40, 1885–
1898; (d) C. S. Yeung and V. M. Dong, Chem. Rev., 2011,
A. F. Stepan and J.-Q. Yu, J. Am. Chem. Soc., 2013, 135,
7567–7571.
111, 1215–1292; (e) J. Yamaguchi, A. D. Yamaguchi and 12 (a) L. Ackermann, E. Diers and A. Manvar, Org. Lett., 2012,
K. Itami, Angew. Chem., Int. Ed., 2012, 51, 8960–9009.
2 (a) T. W. Lyons and M. S. Sanford, Chem. Rev., 2010, 110,
14, 1154–1157; (b) W. Ma and L. Ackermann, Chem.–Eur. J.,
2013, 19, 13925–13928.
1147–1169; (b) S. R. Neufeldt and M. S. Sanford, Acc. Chem. 13 Also noteworthy is the use of Rh catalysis with phosphinite
Res., 2012, 45, 936–946; (c) Y.-H. Zhang, G.-F. Shi and
J.-Q. Yu, in Comprehensive Organic Synthesis, ed. P. Knochel
and G. A. Molander, Elsevier, Amsterdam, 2nd edn, 2014,
vol. 3, pp. 1101–1209.
species that dynamically exchange with phenols to provide
in situ directing groups. For key examples, see: (a)
L. N. Lewis and J. F. Smith, J. Am. Chem. Soc., 1986, 108,
2728–2735; (b) S. Oi, S.-i. Watanabe, S. Fukita and
Y. Inoue, Tetrahedron Lett., 2003, 44, 8665–8668; (c)
R. B. Bedford, S. J. Coles, M. B. Hursthouse and
M. E. Limmert, Angew. Chem., Int. Ed., 2003, 42, 112–114;
(d) J. C. Lewis, J. Wu, R. G. Bergman and J. A. Ellman,
3 For
a
review on relevant strategies toward C–H
functionalization of alcohol substrates, see, F. Mo,
J. R. Tabor and G. Dong, Chem. Lett., 2014, 43, 264–271.
4 (a) Y. Lu, D.-H. Wang, K. M. Engle and J.-Q. Yu, J. Am. Chem.
Soc., 2010, 132, 5916–5921; (b) X. Wang, Y. Lu, H.-X. Dai and
J.-Q. Yu, J. Am. Chem. Soc., 2010, 132, 12203–12205; (c) Y. Lu,
´
Organometallics, 2005, 24, 5737–5746; (e) M. C. Carrion and
D. J. Cole-Hamilton, Chem. Commun., 2006, 4527–4529.
D. Leow, X. Wang, K. M. Engle and J.-Q. Yu, Chem. Sci., 2011, 14 (a) E. M. Simmons and J. F. Hartwig, J. Am. Chem. Soc., 2010,
2, 967–971; (d) K. Morimoto, K. Hirano, T. Satoh and
M. Miura, J. Org. Chem., 2011, 76, 9548–9551; (e)
S. R. Kandukuri, L.-Y. Jiao, A. B. Machotta and
132, 17092–17095; (b) For
a
related case in the
functionalization of sp3 C–H bonds, see: E. M. Simmons
and J. F. Hartwig, Nature, 2012, 483, 70–73.
M. Oestreich, Adv. Synth. Catal., 2014, 356, 1597–1609; (f) 15 S. Lee, H. Lee and K. L. Tan, J. Am. Chem. Soc., 2013, 135,
S. Nakanowatari and L. Ackermann, Chem.–Eur. J., 2014,
20, 5409–5413.
5 For recent reviews on functional group surrogates for C–H
18778–18781.
16 L. Chu, M. Shang, K. Tanaka, Q. Chen, N. Pissarnitski,
E. Streckfuss and J.-Q. Yu, ACS Cent. Sci., 2015, 1, 394–399.
functionalization, see: (a) G. Rousseau and B. Breit, Angew. 17 (a) K. Guo, X. Chen, M. Guan and Y. Zhao, Org. Lett., 2015,
Chem., Int. Ed., 2011, 50, 2450–2494; (b) F. Zhang and
D. R. Spring, Chem. Soc. Rev., 2014, 43, 6906–6919; (c)
17, 1802–1805; (b) K. Guo, X. Chen, J. Zhang and Y. Zhao,
Chem.–Eur. J., 2015, 21, 17474–17478.
C. Wang and Y. Huang, Synlett, 2013, 24, 145–149; (d) 18 Z. Ren, J. E. Schulz and G. Dong, Org. Lett., 2015, 17, 2696–
E. M. Ferreira, Nat. Chem., 2014, 6, 94–96; (e) R. K. Rit,
2699.
M. R. Yadav, K. Ghosh and A. K. Sahoo, Tetrahedron, 2015, 19 The three steps involve Mitsunobu reaction with N-
71, 4450–4459.
hydroxyphthalimide, cleavage of the imide, and carbonyl
condensation. The overall transformation can be
conveniently accomplished in one pot; see ref. 17.
Alternatively,this net transformation can be accomplished
in two steps using Ellman's oxaziridine for direct O-
amination, but the yields are generally lower and this
option is less frequently employed.
6 For select examples of this strategy in sp3 C–H
functionalization using Pd catalysis, see: (a) Z. Ren, F. Mo
and G. Dong, J. Am. Chem. Soc., 2012, 134, 16991–16994; (b)
P. E. Gormisky and M. C. White, J. Am. Chem. Soc., 2011,
133, 12584–12589; (c) K. J. Fraunhoffer and M. C. White, J.
Am. Chem. Soc., 2007, 129, 7274–7276; (d) G. T. Rice and
M. C. White, J. Am. Chem. Soc., 2009, 131, 11707–11711.
7 Di-tert-butyl-silanol: (a) C. Huang, B. Chattopadhyay and
V. Gevorgyan, J. Am. Chem. Soc., 2011, 133, 12406–12409;
(b) C. Huang, N. Ghavtadze, B. Chattopadhyay and
V. Gevorgyan, J. Am. Chem. Soc., 2011, 133, 17630–17633;
20 (a) K. M. Engle, D.-H. Wang and J.-Q. Yu, J. Am. Chem. Soc.,
2010, 132, 14137–14151; (b) D. Leow, G. Li, T.-S. Mei and
J.-Q. Yu, Nature, 2012, 486, 518–522.
1986 | Chem. Sci., 2016, 7, 1982–1987
This journal is © The Royal Society of Chemistry 2016