423
33. Ghosh KK, Uttry A, Koldemir A, Ong M, van Gemmeren M (2019) Direct β-C(sp
3 )–H acetoxylation of aliphatic carboxylic acids. Org Lett 21:7154–7157
34. Giri R, Liang J, Lei JG, Li JJ, Wang DH, Chen X, Naggar IC, Guo C, Foxman BM, Yu
JQ (2005) Pd‐catalyzed stereoselective oxidation of methyl groups by inexpensive oxidants
under mild conditions: a dual role for carboxylic anhydrides in catalytic C-H bond oxidation.
Angew Chem Int Ed 44:7420–7424
35. He J, Shigenari T, Yu JQ (2015) Palladium(0)/PAr 3 ‐catalyzed intermolecular amination of
C(sp
3 )–H bonds: synthesis of β‐amino acids. Angew Chem Int Ed 54:6545–6549
36. Wasa M, Engle KM, Yu JQ (2009) Pd(0)/PR 3 -catalyzed intermolecular arylation of sp
3
C−H
bonds. J Am Chem Soc 131:9886–9887
37. Tan Y, Hartwig JF (2010) Palladium-catalyzed amination of aromatic C−H bonds with oxime
esters. J Am Chem Soc 132:3676–3677
38. Fürstner A, Seidel G (2002) Microwave-assisted synthesis of pinacol boronates from aryl
chlorides catalyzed by a palladium/imidazolium salt system. Org Lett 4:541–543
39. Billingsley KL, Barder TE, Buchwald SL (2007) Palladium‐catalyzed borylation of aryl chlorides: Scope, applications, and computational studies. Angew Chem Int Ed 46:5359–5363
40. Billingsley KL, Buchwald SL (2008) An improved system for the palladium-catalyzed borylation of aryl halides with pinacol borane. J Org Chem 73:5589–5591
41. Molander GA, Trice SLJ, Dreher SD (2010) Palladium-catalyzed, direct boronic acid synthesis from aryl chlorides: A simplified route to diverse boronate ester derivatives. J Am Chem
Soc 132:17701–17703
42. Dai HX, Yu JQ (2012) Pd-catalyzed oxidative ortho-C–H borylation of arenes. J Am Chem
Soc 134:134–137
43. Zhang LS, Chen G, Wang X, Guo QY, Zhang XS, Pan F, Chen K, Shi ZJ (2014) Direct
borylation of primary C–H bonds in functionalized molecules by palladium catalysis. Angew
Chem Int Ed 53:3899–3903
44. He J, Jiang H, Takise R, Zhu RY, Chen G, Dai HX, Murali Dhar TG, Shi J, Zhang H, Cheng
PTW, Yu JQ (2016) Ligand‐promoted borylation of C(sp
3 )–H bonds with palladium(II) catalysts. Angew Chem Int Ed 55:785–789
45. He J, Shao Q, Wu Q, Yu JQ (2017) Pd(II)-Catalyzed enantioselective C(sp
3
)–H borylation. J
Am Chem Soc 139:3344–3347
46. Shi Y, Gao Q, Xu S (2019) Chiral bidentate boryl ligand enabled iridium-catalyzed enantioselective C(sp
3 )–H borylation of cyclopropanes. J Am Chem Soc 141:10599–10604
47. Murakami R, Iwai T, Sawamura M (2016) Site-selective and stereoselective C(sp
3
)-H borylation of alkyl side chains of 1,3-azoles with a silica-supported monophosphine-iridium catalyst. Synlett 27:1187–1192
48. Giri R, Chen X, Yu JQ (2005) Palladium‐catalyzed asymmetric iodination of unactivated
C–H bonds under mild conditions. Angew Chem Int Ed 44:2112–2115
49. He J, Li S, Deng Y, Fu H, Laforteza BN, Spangler JE, Homs A, Yu JQ (2014) Ligandcontrolled C(sp
3 )–H arylation and olefination in synthesis of unnatural chiral α–amino acids.
Science 343:1216–1220
50. Zhu RY, Saint-Denis TG, Shao Y, He J, Sieber JD, Senanayake CH, Yu JQ (2017) Ligandenabled Pd(II)-catalyzed bromination and iodination of C(sp
3 )–H bonds. J Am Chem Soc
139:5724–5727
51. Zhu RY, Tanaka K, Li GC, He J, Fu HY, Li SH, Yu JQ (2015) Ligand-enabled stereoselective
β-C(sp
3 )–H fluorination: Synthesis of unnatural enantiopure anti-β-fluoro-α-amino acids. J
Am Chem Soc 137:7067–7070
52. Zaitsev VG, Shabashov D, Daugulis O (2005) Highly regioselective arylation of sp
3
C−H
bonds catalyzed by palladium acetate. J Am Chem Soc 127:13154–13155
53. Rouquet G, Chatani N (2013) Catalytic functionalization of C(sp
2
)–H and C(sp
3
)–H bonds by
using bidentate directing groups. Angew Chem Int Ed 52:11726–11743
54. Castro LCM, Chatani N (2015) Nickel catalysts/N,N′-bidentate directing groups: an excellent partnership in directed C–H activation reactions. Chem Lett 44:410–421
C(sp
3
)–H Bond Hetero-functionalization of Aliphatic Carboxylic Acid Equivalents…
33. Ghosh KK, Uttry A, Koldemir A, Ong M, van Gemmeren M (2019) Direct β-C(sp
3 )–H acetoxylation of aliphatic carboxylic acids. Org Lett 21:7154–7157
34. Giri R, Liang J, Lei JG, Li JJ, Wang DH, Chen X, Naggar IC, Guo C, Foxman BM, Yu
JQ (2005) Pd‐catalyzed stereoselective oxidation of methyl groups by inexpensive oxidants
under mild conditions: a dual role for carboxylic anhydrides in catalytic C-H bond oxidation.
Angew Chem Int Ed 44:7420–7424
35. He J, Shigenari T, Yu JQ (2015) Palladium(0)/PAr 3 ‐catalyzed intermolecular amination of
C(sp
3 )–H bonds: synthesis of β‐amino acids. Angew Chem Int Ed 54:6545–6549
36. Wasa M, Engle KM, Yu JQ (2009) Pd(0)/PR 3 -catalyzed intermolecular arylation of sp
3
C−H
bonds. J Am Chem Soc 131:9886–9887
37. Tan Y, Hartwig JF (2010) Palladium-catalyzed amination of aromatic C−H bonds with oxime
esters. J Am Chem Soc 132:3676–3677
38. Fürstner A, Seidel G (2002) Microwave-assisted synthesis of pinacol boronates from aryl
chlorides catalyzed by a palladium/imidazolium salt system. Org Lett 4:541–543
39. Billingsley KL, Barder TE, Buchwald SL (2007) Palladium‐catalyzed borylation of aryl chlorides: Scope, applications, and computational studies. Angew Chem Int Ed 46:5359–5363
40. Billingsley KL, Buchwald SL (2008) An improved system for the palladium-catalyzed borylation of aryl halides with pinacol borane. J Org Chem 73:5589–5591
41. Molander GA, Trice SLJ, Dreher SD (2010) Palladium-catalyzed, direct boronic acid synthesis from aryl chlorides: A simplified route to diverse boronate ester derivatives. J Am Chem
Soc 132:17701–17703
42. Dai HX, Yu JQ (2012) Pd-catalyzed oxidative ortho-C–H borylation of arenes. J Am Chem
Soc 134:134–137
43. Zhang LS, Chen G, Wang X, Guo QY, Zhang XS, Pan F, Chen K, Shi ZJ (2014) Direct
borylation of primary C–H bonds in functionalized molecules by palladium catalysis. Angew
Chem Int Ed 53:3899–3903
44. He J, Jiang H, Takise R, Zhu RY, Chen G, Dai HX, Murali Dhar TG, Shi J, Zhang H, Cheng
PTW, Yu JQ (2016) Ligand‐promoted borylation of C(sp
3 )–H bonds with palladium(II) catalysts. Angew Chem Int Ed 55:785–789
45. He J, Shao Q, Wu Q, Yu JQ (2017) Pd(II)-Catalyzed enantioselective C(sp
3
)–H borylation. J
Am Chem Soc 139:3344–3347
46. Shi Y, Gao Q, Xu S (2019) Chiral bidentate boryl ligand enabled iridium-catalyzed enantioselective C(sp
3 )–H borylation of cyclopropanes. J Am Chem Soc 141:10599–10604
47. Murakami R, Iwai T, Sawamura M (2016) Site-selective and stereoselective C(sp
3
)-H borylation of alkyl side chains of 1,3-azoles with a silica-supported monophosphine-iridium catalyst. Synlett 27:1187–1192
48. Giri R, Chen X, Yu JQ (2005) Palladium‐catalyzed asymmetric iodination of unactivated
C–H bonds under mild conditions. Angew Chem Int Ed 44:2112–2115
49. He J, Li S, Deng Y, Fu H, Laforteza BN, Spangler JE, Homs A, Yu JQ (2014) Ligandcontrolled C(sp
3 )–H arylation and olefination in synthesis of unnatural chiral α–amino acids.
Science 343:1216–1220
50. Zhu RY, Saint-Denis TG, Shao Y, He J, Sieber JD, Senanayake CH, Yu JQ (2017) Ligandenabled Pd(II)-catalyzed bromination and iodination of C(sp
3 )–H bonds. J Am Chem Soc
139:5724–5727
51. Zhu RY, Tanaka K, Li GC, He J, Fu HY, Li SH, Yu JQ (2015) Ligand-enabled stereoselective
β-C(sp
3 )–H fluorination: Synthesis of unnatural enantiopure anti-β-fluoro-α-amino acids. J
Am Chem Soc 137:7067–7070
52. Zaitsev VG, Shabashov D, Daugulis O (2005) Highly regioselective arylation of sp
3
C−H
bonds catalyzed by palladium acetate. J Am Chem Soc 127:13154–13155
53. Rouquet G, Chatani N (2013) Catalytic functionalization of C(sp
2
)–H and C(sp
3
)–H bonds by
using bidentate directing groups. Angew Chem Int Ed 52:11726–11743
54. Castro LCM, Chatani N (2015) Nickel catalysts/N,N′-bidentate directing groups: an excellent partnership in directed C–H activation reactions. Chem Lett 44:410–421
C(sp
3
)–H Bond Hetero-functionalization of Aliphatic Carboxylic Acid Equivalents…