Biomedical Engineering Reference
In-Depth Information
Ru(I)-catalyzed
ortho-directed arylation
F 3 C
Pd(0)-catalyzed
indolizine direct arylation
HO
N
N
O
OMe
N
O
N
N
NC
F 3 C
Me
Me
F
Me
F
CF 3
F
GABAA agonist 122 [100]
Anacetrapib 123 [101]
SCHEME 1.31
Structures of a GABA A agonist and anacetrapib.
These applications further highlight the remarkable and exciting growth in the area of
C-H bond functionalization.
REFERENCES
1. For selected general reviews on catalytic transformations at C-H bonds for C-C and C-X bond
formation, see (a) G. Dyker, Angew. Chem., Int. Ed.
1999 , 38 , 1698-1712; (b) V. Ritleng, C. Sirlin, M.
Pfeffer, Chem. Rev.
2003 , 345 ,
1077-1101; (d) G. Dyker (Ed.), Handbook of C-H Transformations , Wiley-VCH, Weinheim, 2005 ;
(e) A. R. Dick, M. S. Sanford, Tetrahedron
2002 , 102 , 1731-1769; (c) F. Kakiuchi, N. Chatani, Adv. Synth. Catal.
2006
, 62 , 2439-2463; (f) I. V. Seregin, V. Gevorgyan,
Chem. Soc. Rev.
2007
, 36 , 1173-1193; (g) X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew.
Chem., Int. Ed.
2009
, 48 , 5094-5115; (h) P. Thansandote, M. Lautens, Chem. Eur. J.
2009
, 15 ,
, 38 ,
3242-3272; (j) A. A. Kulkarni, O. Daugulis, Synthesis 2009 , 4087-4109; (k) R. Jazzar, J. Hitce, A.
Renaudat, J. Sofack-Kreutzer, O. Baudoin, Chem. Eur. J. 2010 , 16 , 2654-2672; (l) T. W. Lyons, M. S.
Sanford, Chem. Rev. 2010 , 110 , 1147-1169; (m) H. M. L. Davies, A. R. Dick, Top. Curr. Chem. 2010 ,
292 , 1-383.
2. Y.-R. Luo, Handbook of Bond Dissociation Energies in Organic Compounds , CRC Press, Boca
Raton, 2003 .
3. For a review, see K. Godula, D. Sames, Science 2006 , 312 , 67-72.
4. For selected reviews that highlight these mechanistic differences, see R. H. Crabtree, J. Chem. Soc.,
Dalton Trans. 2001 , 2437-2450 (see also Ref. [1e]).
5. For selected reviews, see (a) H. M. L. Davies, R. E. J. Beckwith, Chem. Rev. 2003 , 103 , 2861-2903;
(b)L.Que,Jr.,W.B.Tolman, Nature 2008 , 455 , 333-340; (c) H. M. L. Davies, J. R. Manning,
Nature 2008 , 451 , 417-424; (d) M. M. Diaz-Requejo, P. J. P ´ rez, Chem. Rev. 2008 , 108 ,
3379-3394; (e) F. Collet, R. H. Dodd, P. Dauban, Chem. Commun. 2009 , 5061-5074; (f) M. P.
Doyle, R. Duffy, M. Ratnikov, L. Zhou, Chem. Rev. 2010 , 110 , 704-724; (g) D. N. Zalatan, J. Du
Bois, Top. Curr. Chem. 2010 , 292 , 347-378; (h) A. Gunay, K. H. Theopold, Chem. Rev. 2010 , 110 ,
1060-1081.
6. For selected examples of the use of C-H bond insertion (outer sphere mechanism) in natural
product synthesis, see (a) J. W. Bode, M. P. Doyle, M. N. Protopopova, Q.-L. Zhou, J. Org.
Chem.
5874-5883; (i) R. Giri, B.-F. Shi, K. M. Engle, N. Maugel, J.-Q. Yu, Chem. Soc. Rev.
2009
1996 , 61 , 9146-9155; (b) P. M. When, J. Du Bois, J. Am. Chem. Soc.
2002 , 124 ,
12950-12951; (c) H. M. L. Davies, Q. Jin, Tetrahedron: Asymmetry
2003 , 14 , 941-949; (d) A.
Hinman, J. Du Bois, J. Am. Chem. Soc.
2003 , 125 , 11510-11511; (e) H. M. L. Davies, X. Dai,
M. S. Long, J. Am. Chem. Soc.
2006 , 128 , 2485-2490; (f) M. S. Chen, M. C. White, Science
2007
, 318 , 783-787; (g) H. M. L. Davies, J. R. Denton, Chem. Soc. Rev.
2009
, 38 , 3061-3071
and references therein.
7. For selected reviews related to themechanismof transformations at C-Hbonds proceeding through an
inner sphere pathway, see (a) A. D Ryabov, Chem. Rev.
, 90 , 403-424; (b) A. E. Shilov, G. B.
Shul'pin, Chem. Rev. 1997 , 97 , 2879-2932; (c) R. H. Crabtree, J. Organomet. Chem. 2004 , 689 ,
4083-4091; (d) Y. Boutadla, D. L. Davies, S. A. Macgregor, A. I. Poblador-Bahamonde, Dalton
1990
 
Search WWH ::




Custom Search