6. Reichelt A, Martin SF (2006) Synthesis and properties of cyclopropane-derived
peptidomimetics. Acc Chem Res 39(7):433–442
7. Taylor RD, MacCoss M, Lawson ADG (2014) Rings in drugs. J Med Chem 57(14):5845–5859
8. Lebel H, Marcoux J-F, Molinaro C, Charette AB (2003) Stereoselective cyclopropanation
reactions. Chem Rev 103(4):977–1050
9. Pellissier H (2008) Recent developments in asymmetric cyclopropanation. Tetrahedron 64
(30–31):7041–7095
10. Gagnon A, Duplessis M, Fader L (2010) Arylcyclopropanes: properties, synthesis and use in
medicinal chemistry. Org Prep Proc Int 42:1–73
11. Rubin M, Rubina M, Gevorgyan V (2007) Transition metal chemistry of cyclopropenes and
cyclopropanes. Chem Rev 107(7):3117–3179
12. Ackermann L (2010) Metal-catalyzed direct alkylations of (hetero)arenes via C-H bond
cleavages with unactivated alkyl halides. Chem Commun 46(27):4866–4877
13. Engle KM, Mei T-S, Wasa M, Yu J-Q (2012) Weak coordination as a powerful means for
developing broadly useful C–H functionalization reactions. Acc Chem Res 45(6):788–802
14. Neufeldt SR, Sanford MS (2012) Controlling site selectivity in palladium-catalyzed C–H bond
functionalization. Acc Chem Res 45(6):936–946
15. Lyons TW, Sanford MS (2010) Palladium-catalyzed ligand-directed C–H functionalization
reactions. Chem Rev 110(2):1147–1169
16. Alberico D, Scott ME, Lautens M (2007) Aryl–aryl bond formation by transition-metalcatalyzed direct arylation. Chem Rev 107(1):174–238
17. Eaton PE, Daniels RG, Casucci D, Cunkle GT, Engel P (1987) Amide activation for cyclopropane ortho-lithiation. J Org Chem 52(10):2100–2102
18. Zhang M-X, Eaton PE (2002) BuMgNiPr2: a new base for stoichiometric, position-selective
deprotonation of cyclopropane carboxamides and other weak CH acids. Angew Chem Int Ed
41(12):2169–2171
19. Giri R, Chen X, Yu J-Q (2005) Palladium-catalyzed asymmetric iodination of unactivated C–
H bonds under mild conditions. Angew Chem Int Ed 44(14):2112–2115
20. Wang D-H, Wasa M, Giri R, Yu J-Q (2008) Pd(II)-catalyzed cross-coupling of sp3 C–H bonds
with sp2 and sp3 boronic acids using air as the oxidant. J Am Chem Soc 130(23):7190–7191
21. Wasa M, Engle KM, Yu J-Q (2010) Pd(II)-catalyzed olefination of sp3 C–H bonds. J Am
Chem Soc 132(11):3680–3681
22. Yoo EJ, Wasa M, Yu J-Q (2010) Pd(II)-catalyzed carbonylation of C(sp3)–H bonds: a new
entry to 1,4-dicarbonyl compounds. J Am Chem Soc 132(49):17378–17380
23. Hasegawa N, Shibata K, Charra V, Inoue S, Fukumoto Y, Chatani N (2013) Rutheniumcatalyzed cyclocarbonylation of aliphatic amides through the regioselective activation of
unactivated C(sp3)–H bonds. Tetrahedron 69(22):4466–4472
24. Kubota A, Sanford MS (2011) Palladium-catalyzed ligand-directed oxidative functionalization
of cyclopropanes. Synthesis 2011(16):2579–2589
25. Stowers KJ, Fortner KC, Sanford MS (2011) Aerobic Pd-catalyzed sp3 C–H olefination: a
route to both N-heterocyclic scaffolds and alkenes. J Am Chem Soc 133(17):6541–6544
26. Rousseaux S, Liegault B, Fagnou K (2012) Palladium(0)-catalyzed cyclopropane C-H bond
functionalization: synthesis of quinoline and tetrahydroquinoline derivatives. Chem Sci 3
(1):244–248
27. Dos Santos A, El Kaı ¨m L, Grimaud L, Ramozzi R (2012) Palladium-catalyzed ring opening of
aminocyclopropyl Ugi adducts. Synlett 2012(3):438–442
28. Rosa D, Orellana A (2011) Palladium-catalyzed cross-coupling of cyclopropanols with aryl
halides under mild conditions. Org Lett 13(1):110–113
29. He Z, Yudin AK (2006) Palladium-catalyzed oxidative activation of arylcyclopropanes. Org
Lett 8(25):5829–5832
30. Ladd CL, Roman DS, Charette AB (2013) Palladium-catalyzed ring-opening of cyclopropyl
benzamides: synthesis of benzo[c]azepine-1-ones via C(sp3)–H functionalization. Tetrahedron 69(22):4479–4487
Catalytic C–H Bond Functionalization of Cyclopropane Derivatives
111
peptidomimetics. Acc Chem Res 39(7):433–442
7. Taylor RD, MacCoss M, Lawson ADG (2014) Rings in drugs. J Med Chem 57(14):5845–5859
8. Lebel H, Marcoux J-F, Molinaro C, Charette AB (2003) Stereoselective cyclopropanation
reactions. Chem Rev 103(4):977–1050
9. Pellissier H (2008) Recent developments in asymmetric cyclopropanation. Tetrahedron 64
(30–31):7041–7095
10. Gagnon A, Duplessis M, Fader L (2010) Arylcyclopropanes: properties, synthesis and use in
medicinal chemistry. Org Prep Proc Int 42:1–73
11. Rubin M, Rubina M, Gevorgyan V (2007) Transition metal chemistry of cyclopropenes and
cyclopropanes. Chem Rev 107(7):3117–3179
12. Ackermann L (2010) Metal-catalyzed direct alkylations of (hetero)arenes via C-H bond
cleavages with unactivated alkyl halides. Chem Commun 46(27):4866–4877
13. Engle KM, Mei T-S, Wasa M, Yu J-Q (2012) Weak coordination as a powerful means for
developing broadly useful C–H functionalization reactions. Acc Chem Res 45(6):788–802
14. Neufeldt SR, Sanford MS (2012) Controlling site selectivity in palladium-catalyzed C–H bond
functionalization. Acc Chem Res 45(6):936–946
15. Lyons TW, Sanford MS (2010) Palladium-catalyzed ligand-directed C–H functionalization
reactions. Chem Rev 110(2):1147–1169
16. Alberico D, Scott ME, Lautens M (2007) Aryl–aryl bond formation by transition-metalcatalyzed direct arylation. Chem Rev 107(1):174–238
17. Eaton PE, Daniels RG, Casucci D, Cunkle GT, Engel P (1987) Amide activation for cyclopropane ortho-lithiation. J Org Chem 52(10):2100–2102
18. Zhang M-X, Eaton PE (2002) BuMgNiPr2: a new base for stoichiometric, position-selective
deprotonation of cyclopropane carboxamides and other weak CH acids. Angew Chem Int Ed
41(12):2169–2171
19. Giri R, Chen X, Yu J-Q (2005) Palladium-catalyzed asymmetric iodination of unactivated C–
H bonds under mild conditions. Angew Chem Int Ed 44(14):2112–2115
20. Wang D-H, Wasa M, Giri R, Yu J-Q (2008) Pd(II)-catalyzed cross-coupling of sp3 C–H bonds
with sp2 and sp3 boronic acids using air as the oxidant. J Am Chem Soc 130(23):7190–7191
21. Wasa M, Engle KM, Yu J-Q (2010) Pd(II)-catalyzed olefination of sp3 C–H bonds. J Am
Chem Soc 132(11):3680–3681
22. Yoo EJ, Wasa M, Yu J-Q (2010) Pd(II)-catalyzed carbonylation of C(sp3)–H bonds: a new
entry to 1,4-dicarbonyl compounds. J Am Chem Soc 132(49):17378–17380
23. Hasegawa N, Shibata K, Charra V, Inoue S, Fukumoto Y, Chatani N (2013) Rutheniumcatalyzed cyclocarbonylation of aliphatic amides through the regioselective activation of
unactivated C(sp3)–H bonds. Tetrahedron 69(22):4466–4472
24. Kubota A, Sanford MS (2011) Palladium-catalyzed ligand-directed oxidative functionalization
of cyclopropanes. Synthesis 2011(16):2579–2589
25. Stowers KJ, Fortner KC, Sanford MS (2011) Aerobic Pd-catalyzed sp3 C–H olefination: a
route to both N-heterocyclic scaffolds and alkenes. J Am Chem Soc 133(17):6541–6544
26. Rousseaux S, Liegault B, Fagnou K (2012) Palladium(0)-catalyzed cyclopropane C-H bond
functionalization: synthesis of quinoline and tetrahydroquinoline derivatives. Chem Sci 3
(1):244–248
27. Dos Santos A, El Kaı ¨m L, Grimaud L, Ramozzi R (2012) Palladium-catalyzed ring opening of
aminocyclopropyl Ugi adducts. Synlett 2012(3):438–442
28. Rosa D, Orellana A (2011) Palladium-catalyzed cross-coupling of cyclopropanols with aryl
halides under mild conditions. Org Lett 13(1):110–113
29. He Z, Yudin AK (2006) Palladium-catalyzed oxidative activation of arylcyclopropanes. Org
Lett 8(25):5829–5832
30. Ladd CL, Roman DS, Charette AB (2013) Palladium-catalyzed ring-opening of cyclopropyl
benzamides: synthesis of benzo[c]azepine-1-ones via C(sp3)–H functionalization. Tetrahedron 69(22):4479–4487
Catalytic C–H Bond Functionalization of Cyclopropane Derivatives
111