16
1 Theoretical View of Rh-Catalyzed C–H Functionalization
91. Su B, Cao ZC, Shi ZJ (2015) Exploration of earth-abundant transition metals (Fe Co, and Ni)
as catalysts in unreactive chemical bond activations. Acc Chem Res 48:886–896
92. Wang F, Chen P, Liu G (2018) Copper-catalyzed radical relay for asymmetric radical
transformations. Acc Chem Res 51:2036–2046
93. Colby DA, Bergman RG, Ellman JA (2010) Rhodium-catalyzed C–C bond formation via
heteroatom-directed C–H bond activation. Chem Rev 110:624–655
94. Colby DA, Tsai AS, Bergman RG, Ellman JA (2012) Rhodium catalyzed chelation-assisted
C–H bond functionalization reactions. Acc Chem Res 45:814–825
95. Berman AM, Lewis JC, Bergman RG, Ellman JA (2008) Rh(I)-catalyzed direct arylation of
pyridines and quinolines. J Am Chem Soc 130:14926–14927
96. Colby DA, Bergman RG, Ellman JA (2008) Synthesis of dihydropyridines and pyridines from
imines and alkynes via C–H activation. J Am Chem Soc 130:3645–3651
97. Hesp KD, Bergman RG, Ellman JA (2011) Expedient synthesis of N-acyl anthranilamides
and beta-enamine amides by the Rh(III)-catalyzed amidation of aryl and vinyl C–H bonds
with isocyanates. J Am Chem Soc 133:11430–11433
98. Lewis JC, Bergman RG, Ellman JA (2007) Rh(I)-catalyzed alkylation of quinolines and
pyridines via C–H bond activation. J Am Chem Soc 129:5332–5333
99. Lewis JC, Berman AM, Bergman RG, Ellman JA (2008) Rh(I)-catalyzed arylation of heterocycles via C–H bond activation: expanded scope through mechanistic insight. J Am Chem
Soc 130:2493–2500
100. Lian Y, Bergman RG, Lavis LD, Ellman JA (2013) Rhodium(III)-catalyzed indazole synthesis
by C–H bond functionalization and cyclative capture. J Am Chem Soc 135:7122–7125
101. Tsai AS, Tauchert ME, Bergman RG, Ellman JA (2011) Rhodium(III)-catalyzed arylation of
Boc-imines via C–H bond functionalization. J Am Chem Soc 133:1248–1250
102. Wilson RM, Thalji RK, Bergman RG, Ellman JA (2006) Enantioselective synthesis of a PKC
inhibitor via catalytic C–H bond activation. Org Lett 8:1745–1747
103. O’Malley SJ, Tan KL, Watzke A, Bergman RG, Ellman JA (2005) Total synthesis of (+)lithospermic acid by asymmetric intramolecular alkylation via catalytic C–H bond activation.
J Am Chem Soc 127:13496–13497
104. Schroder N, Lied F, Glorius F (2015) Dual role of Rh(III) catalyst enables regioselective
halogenation of (electron-rich) heterocycles. J Am Chem Soc 137:1448–1451
105. Song G, Li X (2015) Substrate activation strategies in rhodium(III)-catalyzed selective
functionalization of arenes. Acc Chem Res 48:1007–1020
106. Zhang X, Qi Z, Li X (2014) Rhodium(III)-catalyzed C–C and C–O coupling of quinoline
N-oxides with alkynes: combination of C–H activation with O-atom transfer. Angew Chem
Int Ed 53:10794–10798
107. Shin K, Kim H, Chang S (2015) Transition-metal-catalyzed C-N bond forming reactions using
organic azides as the nitrogen source: a journey for the mild and versatile C–H amination.
Acc Chem Res 48:1040–1052
108. Ye B, Cramer N (2012) Chiral cyclopentadienyl ligands as stereocontrolling element in
asymmetric C–H functionalization. Science 338:504–506
109. Hyster TK, Rovis T (2010) Rhodium-catalyzed oxidative cycloaddition of benzamides and
alkynes via C–H/N–H activation. J Am Chem Soc 132:10565–10569
110. Hyster TK, Ruhl KE, Rovis T (2013) A coupling of benzamides and donor/acceptor diazo
compounds to form gamma-lactams via Rh(III)-catalyzed C–H activation. J Am Chem Soc
135:5364–5367
111. Piou T, Rovis T (2018) Electronic and steric tuning of a prototypical piano stool complex:
Rh(III) catalysis for C–H functionalization. Acc Chem Res 51:170–180
112. Ackermann L (2011) Carboxylate-assisted transition-metal-catalyzed C–H bond functionalizations: mechanism and scope. Chem Rev 111:1315–1345
113. Ackermann L, Vicente R, Kapdi AR (2009) Transition-metal-catalyzed direct arylation of
(hetero)arenes by C–H bond cleavage. Angew Chem Int Ed 48:9792–9826
114. Dyker G (1999) Transition metal catalyzed coupling reactions under C–H activation. Angew
Chem Int Ed 38:1698–1712
1 Theoretical View of Rh-Catalyzed C–H Functionalization
91. Su B, Cao ZC, Shi ZJ (2015) Exploration of earth-abundant transition metals (Fe Co, and Ni)
as catalysts in unreactive chemical bond activations. Acc Chem Res 48:886–896
92. Wang F, Chen P, Liu G (2018) Copper-catalyzed radical relay for asymmetric radical
transformations. Acc Chem Res 51:2036–2046
93. Colby DA, Bergman RG, Ellman JA (2010) Rhodium-catalyzed C–C bond formation via
heteroatom-directed C–H bond activation. Chem Rev 110:624–655
94. Colby DA, Tsai AS, Bergman RG, Ellman JA (2012) Rhodium catalyzed chelation-assisted
C–H bond functionalization reactions. Acc Chem Res 45:814–825
95. Berman AM, Lewis JC, Bergman RG, Ellman JA (2008) Rh(I)-catalyzed direct arylation of
pyridines and quinolines. J Am Chem Soc 130:14926–14927
96. Colby DA, Bergman RG, Ellman JA (2008) Synthesis of dihydropyridines and pyridines from
imines and alkynes via C–H activation. J Am Chem Soc 130:3645–3651
97. Hesp KD, Bergman RG, Ellman JA (2011) Expedient synthesis of N-acyl anthranilamides
and beta-enamine amides by the Rh(III)-catalyzed amidation of aryl and vinyl C–H bonds
with isocyanates. J Am Chem Soc 133:11430–11433
98. Lewis JC, Bergman RG, Ellman JA (2007) Rh(I)-catalyzed alkylation of quinolines and
pyridines via C–H bond activation. J Am Chem Soc 129:5332–5333
99. Lewis JC, Berman AM, Bergman RG, Ellman JA (2008) Rh(I)-catalyzed arylation of heterocycles via C–H bond activation: expanded scope through mechanistic insight. J Am Chem
Soc 130:2493–2500
100. Lian Y, Bergman RG, Lavis LD, Ellman JA (2013) Rhodium(III)-catalyzed indazole synthesis
by C–H bond functionalization and cyclative capture. J Am Chem Soc 135:7122–7125
101. Tsai AS, Tauchert ME, Bergman RG, Ellman JA (2011) Rhodium(III)-catalyzed arylation of
Boc-imines via C–H bond functionalization. J Am Chem Soc 133:1248–1250
102. Wilson RM, Thalji RK, Bergman RG, Ellman JA (2006) Enantioselective synthesis of a PKC
inhibitor via catalytic C–H bond activation. Org Lett 8:1745–1747
103. O’Malley SJ, Tan KL, Watzke A, Bergman RG, Ellman JA (2005) Total synthesis of (+)lithospermic acid by asymmetric intramolecular alkylation via catalytic C–H bond activation.
J Am Chem Soc 127:13496–13497
104. Schroder N, Lied F, Glorius F (2015) Dual role of Rh(III) catalyst enables regioselective
halogenation of (electron-rich) heterocycles. J Am Chem Soc 137:1448–1451
105. Song G, Li X (2015) Substrate activation strategies in rhodium(III)-catalyzed selective
functionalization of arenes. Acc Chem Res 48:1007–1020
106. Zhang X, Qi Z, Li X (2014) Rhodium(III)-catalyzed C–C and C–O coupling of quinoline
N-oxides with alkynes: combination of C–H activation with O-atom transfer. Angew Chem
Int Ed 53:10794–10798
107. Shin K, Kim H, Chang S (2015) Transition-metal-catalyzed C-N bond forming reactions using
organic azides as the nitrogen source: a journey for the mild and versatile C–H amination.
Acc Chem Res 48:1040–1052
108. Ye B, Cramer N (2012) Chiral cyclopentadienyl ligands as stereocontrolling element in
asymmetric C–H functionalization. Science 338:504–506
109. Hyster TK, Rovis T (2010) Rhodium-catalyzed oxidative cycloaddition of benzamides and
alkynes via C–H/N–H activation. J Am Chem Soc 132:10565–10569
110. Hyster TK, Ruhl KE, Rovis T (2013) A coupling of benzamides and donor/acceptor diazo
compounds to form gamma-lactams via Rh(III)-catalyzed C–H activation. J Am Chem Soc
135:5364–5367
111. Piou T, Rovis T (2018) Electronic and steric tuning of a prototypical piano stool complex:
Rh(III) catalysis for C–H functionalization. Acc Chem Res 51:170–180
112. Ackermann L (2011) Carboxylate-assisted transition-metal-catalyzed C–H bond functionalizations: mechanism and scope. Chem Rev 111:1315–1345
113. Ackermann L, Vicente R, Kapdi AR (2009) Transition-metal-catalyzed direct arylation of
(hetero)arenes by C–H bond cleavage. Angew Chem Int Ed 48:9792–9826
114. Dyker G (1999) Transition metal catalyzed coupling reactions under C–H activation. Angew
Chem Int Ed 38:1698–1712