31. Ladd CL, Sustac Roman D, Charette AB (2013) Silver-promoted, palladium-catalyzed direct
arylation of cyclopropanes: facile access to spiro 3,3
0 -cyclopropyl oxindoles. Org Lett 15
(6):1350–1353
32. Tsukano C, Okuno M, Takemoto Y (2013) Synthesis of spirooxindoles from carbamoyl
chlorides via cyclopropyl methine C(sp
3
)–H activation using palladium catalyst. Chem Lett
42(7):753–755
33. Saget T, Perez D, Cramer N (2013) Synthesis of functionalized spiroindolines via palladiumcatalyzed methine C–H arylation. Org Lett 15(6):1354–1357
34. Janody S, Jazzar R, Comte A, Holstein PM, Vors J-P, Ford MJ, Baudoin O (2014) Synthesis of
1-indanols and 1-indanamines by intramolecular palladium(0)-catalyzed C(sp3)–H arylation:
impact of conformational effects. Chem Eur J 20(35):11084–11090
35. Alsters PL, Engel PF, Hogerheide MP, Copijn M, Spek AL, van Koten G (1993) Rigid fiveand six-membered C, N, N
0 -bound aryl-, benzyl-, and alkylorganopalladium complexes: sp2
vs. sp3 carbon-hydrogen activation during cyclopalladation and palladium(IV) intermediates
in oxidative addition reactions with dihalogens and alkyl halides. Organometallics 12
(5):1831–1844
36. Shabashov D, Daugulis O (2010) Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon À hydrogen bonds. J Am Chem Soc 132(11):3965–3972
37. Zaitsev VG, Shabashov D, Daugulis O (2005) Highly regioselective arylation of sp3 C–H
bonds catalyzed by palladium acetate. J Am Chem Soc 127(38):13154–13155
38. Rouquet G, Chatani N (2013) Catalytic functionalization of C(sp2)–H and C(sp3)–H bonds by
using bidentate directing groups. Angew Chem Int Ed 52(45):11726–11743
39. Parella R, Gopalakrishnan B, Babu SA (2013) Auxiliary-enabled Pd-catalyzed direct arylation
of methylene C(sp3)–H bond of cyclopropanes: highly diastereoselective assembling of diand trisubstituted cyclopropanecarboxamides. Org Lett 15(13):3238–3241
40. Sustac Roman D, Charette AB (2013) C–H functionalization of cyclopropanes: a practical
approach employing a picolinamide auxiliary. Org Lett 15(17):4394–4397
41. Wei Y, Tang H, Cong X, Rao B, Wu C, Zeng X (2014) Pd(II)-catalyzed intermolecular
arylation of unactivated C(sp3)–H bonds with aryl bromides enabled by 8-aminoquinoline
auxiliary. Org Lett 16(8):2248–2251
42. He G, Chen G (2011) A practical strategy for the structural diversification of aliphatic scaffolds through the palladium-catalyzed picolinamide-directed remote functionalization of
unactivated C(sp3)–H bonds. Angew Chem Int Ed 50(22):5192–5196
43. Hoshiya N, Kobayashi T, Arisawa M, Shuto S (2013) Palladium-catalyzed arylation of
cyclopropanes via directing group-mediated C(sp3)–H bond activation to construct quaternary
carbon centers: synthesis of cis- and trans-1,1,2-trisubstituted chiral cyclopropanes. Org Lett
15(24):6202–6205
44. Wasa M, Chan KSL, Zhang X-G, He J, Miura M, Yu J-Q (2012) Ligand-enabled methylene C
(sp3)–H bond activation with a Pd(II) catalyst. J Am Chem Soc 134(45):18570–18572
45. He J, Li S, Deng Y, Fu H, Laforteza BN, Spangler JE, Homs A, Yu J-Q (2014) Ligandcontrolled C(sp3)–H arylation and olefination in synthesis of unnatural chiral α–amino acids.
Science 343(6176):1216–1220
46. Lauru S, Simpkins NS, Gethin D, Wilson C (2008) Enantioselective synthesis of cyclopropylcarboxamides using s-BuLi-sparteine-mediated metallation. Chem Commun
42:5390–5392
47. Giri R, Shi B-F, Engle KM, Maugel N, Yu J-Q (2009) Transition metal-catalyzed C-H
activation reactions: diastereoselectivity and enantioselectivity. Chem Soc Rev 38
(11):3242–3272
48. Nakanishi M, Katayev D, Besnard C, Ku ¨ndig EP (2011) Fused indolines by palladiumcatalyzed asymmetric C–C coupling involving an unactivated methylene group. Angew
Chem Int Ed 50(32):7438–7441
112
D. Sustac Roman and A.B. Charette
arylation of cyclopropanes: facile access to spiro 3,3
0 -cyclopropyl oxindoles. Org Lett 15
(6):1350–1353
32. Tsukano C, Okuno M, Takemoto Y (2013) Synthesis of spirooxindoles from carbamoyl
chlorides via cyclopropyl methine C(sp
3
)–H activation using palladium catalyst. Chem Lett
42(7):753–755
33. Saget T, Perez D, Cramer N (2013) Synthesis of functionalized spiroindolines via palladiumcatalyzed methine C–H arylation. Org Lett 15(6):1354–1357
34. Janody S, Jazzar R, Comte A, Holstein PM, Vors J-P, Ford MJ, Baudoin O (2014) Synthesis of
1-indanols and 1-indanamines by intramolecular palladium(0)-catalyzed C(sp3)–H arylation:
impact of conformational effects. Chem Eur J 20(35):11084–11090
35. Alsters PL, Engel PF, Hogerheide MP, Copijn M, Spek AL, van Koten G (1993) Rigid fiveand six-membered C, N, N
0 -bound aryl-, benzyl-, and alkylorganopalladium complexes: sp2
vs. sp3 carbon-hydrogen activation during cyclopalladation and palladium(IV) intermediates
in oxidative addition reactions with dihalogens and alkyl halides. Organometallics 12
(5):1831–1844
36. Shabashov D, Daugulis O (2010) Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon À hydrogen bonds. J Am Chem Soc 132(11):3965–3972
37. Zaitsev VG, Shabashov D, Daugulis O (2005) Highly regioselective arylation of sp3 C–H
bonds catalyzed by palladium acetate. J Am Chem Soc 127(38):13154–13155
38. Rouquet G, Chatani N (2013) Catalytic functionalization of C(sp2)–H and C(sp3)–H bonds by
using bidentate directing groups. Angew Chem Int Ed 52(45):11726–11743
39. Parella R, Gopalakrishnan B, Babu SA (2013) Auxiliary-enabled Pd-catalyzed direct arylation
of methylene C(sp3)–H bond of cyclopropanes: highly diastereoselective assembling of diand trisubstituted cyclopropanecarboxamides. Org Lett 15(13):3238–3241
40. Sustac Roman D, Charette AB (2013) C–H functionalization of cyclopropanes: a practical
approach employing a picolinamide auxiliary. Org Lett 15(17):4394–4397
41. Wei Y, Tang H, Cong X, Rao B, Wu C, Zeng X (2014) Pd(II)-catalyzed intermolecular
arylation of unactivated C(sp3)–H bonds with aryl bromides enabled by 8-aminoquinoline
auxiliary. Org Lett 16(8):2248–2251
42. He G, Chen G (2011) A practical strategy for the structural diversification of aliphatic scaffolds through the palladium-catalyzed picolinamide-directed remote functionalization of
unactivated C(sp3)–H bonds. Angew Chem Int Ed 50(22):5192–5196
43. Hoshiya N, Kobayashi T, Arisawa M, Shuto S (2013) Palladium-catalyzed arylation of
cyclopropanes via directing group-mediated C(sp3)–H bond activation to construct quaternary
carbon centers: synthesis of cis- and trans-1,1,2-trisubstituted chiral cyclopropanes. Org Lett
15(24):6202–6205
44. Wasa M, Chan KSL, Zhang X-G, He J, Miura M, Yu J-Q (2012) Ligand-enabled methylene C
(sp3)–H bond activation with a Pd(II) catalyst. J Am Chem Soc 134(45):18570–18572
45. He J, Li S, Deng Y, Fu H, Laforteza BN, Spangler JE, Homs A, Yu J-Q (2014) Ligandcontrolled C(sp3)–H arylation and olefination in synthesis of unnatural chiral α–amino acids.
Science 343(6176):1216–1220
46. Lauru S, Simpkins NS, Gethin D, Wilson C (2008) Enantioselective synthesis of cyclopropylcarboxamides using s-BuLi-sparteine-mediated metallation. Chem Commun
42:5390–5392
47. Giri R, Shi B-F, Engle KM, Maugel N, Yu J-Q (2009) Transition metal-catalyzed C-H
activation reactions: diastereoselectivity and enantioselectivity. Chem Soc Rev 38
(11):3242–3272
48. Nakanishi M, Katayev D, Besnard C, Ku ¨ndig EP (2011) Fused indolines by palladiumcatalyzed asymmetric C–C coupling involving an unactivated methylene group. Angew
Chem Int Ed 50(32):7438–7441
112
D. Sustac Roman and A.B. Charette