18
1 Theoretical View of Rh-Catalyzed C–H Functionalization
137. Wodrich MD, Ye B, Gonthier JF, Corminboeuf C, Cramer N (2014) Ligand-controlled regiodivergent pathways of rhodium(III)-catalyzed dihydroisoquinolone synthesis: experimental and
computational studies of different cyclopentadienyl ligands. Chem A Eur J 20:15409–15418
138. Wu JQ, Zhang SS, Gao H, Qi Z, Zhou CJ, Ji WW, Liu Y, Chen Y, Li Q, Li X, Wang H
(2017) Experimental and theoretical studies on rhodium-catalyzed coupling of benzamides
with 2,2-Difluorovinyl tosylate: diverse synthesis of fluorinated heterocycles. J Am Chem
Soc 139:3537–3545
139. Yang YF, Houk KN, Wu YD (2016) Computational exploration of Rh(III)/Rh(V)
and Rh(III)/Rh(I) catalysis in Rhodium(III)-Catalyzed C–H activation reactions of NPhenoxyacetamides with alkynes. J Am Chem Soc 138:6861–6868
140. Yu S, Liu S, Lan Y, Wan B, Li X (2015) Rhodium-catalyzed C–H activation of phenacyl
ammonium salts assisted by an oxidizing C–N bond: a combination of experimental and
theoretical studies. J Am Chem Soc 137:1623–1631
141. Garcia-Cuadrado D, Braga AA, Maseras F, Echavarren AM (2006) Proton abstraction mechanism for the palladium-catalyzed intramolecular arylation. J Am Chem Soc 128:1066–1067
142. Lafrance M, Rowley CN, Woo TK, Fagnou K (2006) Catalytic intermolecular direct arylation
of perfluorobenzenes. J Am Chem Soc 128:8754–8756
143. Hoyano JK, Graham WAG (1982) Oxidative addition of the carbon-hydrogen bonds of neopentane and cyclohexane to a photochemically generated iridium(I) complex. J Am Chem Soc
104:3723–3725
144. Pivsa-Art S, Satoh T, Kawamura Y, Miura M, Nomura M (1998) Palladium-catalyzed arylation
of azole compounds with aryl halides in the presence of alkali metal carbonates and the use
of copper iodide in the reaction. Bull Chem Soc Japan 71:467–473
145. Watson PL (1983) Methane exchange reactions of lanthanide and early-transition-metal
methyl complexes. J Am Chem Soc 105:6491–6493
146. Guan ZH, Ren ZH, Spinella SM, Yu S, Liang YM, Zhang X (2009) Rhodium-catalyzed
direct oxidative carbonylation of aromatic C–H bond with CO and alcohols. J Am Chem Soc
131:729–733
147. Ishii Y, Chatani N, Kakiuchi F, Murai S (1997) Rhodium-catalyzed reaction of N-(2Pyridinyl)piperazines with CO and ethylene. a novel carbonylation at a C − H bond in the
piperazine ring. Organometallics 16:3615–3622
148. Deng H, Li H, Wang L (2015) A unique alkylation of azobenzenes with allyl acetates by
Rh(III)-Catalyzed C–H functionalization. Org Lett 17:2450–2453
149. Huang L, Wang Q, Qi J, Wu X, Huang K, Jiang H (2013) Rh(iii)-catalyzed ortho-oxidative
alkylation of unactivated arenes with allylic alcohols. Chem Sci 4:2665
150. Shibata K, Chatani N (2014) Rhodium-catalyzed alkylation of C-H bonds in aromatic amides
with alpha, beta-unsaturated esters. Org Lett 16:5148–5151
151. Dateer RB, Chang S (2015) Selective cyclization of arylnitrones to indolines under external
oxidant-free conditions: dual role of Rh(III) catalyst in the C–H activation and oxygen atom
transfer. J Am Chem Soc 137:4908–4911
152. Sharma U, Park Y, Chang S (2014) Rh(III)-catalyzed traceless coupling of quinoline N-oxides
with internal diarylalkynes. J Org Chem 79:9899–9906
153. Chen X, Zheng G, Li Y, Song G, Li X (2017) Rhodium-catalyzed site-selective coupling of
indoles with diazo esters: C4-alkylation versus C2-Annulation. Org Lett 19:6184–6187
154. Wu Y, Chen Z, Yang Y, Zhu W, Zhou B (2018) Rh(III)-catalyzed redox-neutral unsymmetrical
c–h alkylation and amidation reactions of N-Phenoxyacetamides. J Am Chem Soc 140:42–45
155. Qi X, Li Y, Bai R, Lan Y (2017) Mechanism of rhodium-catalyzed C–H functionalization:
advances in theoretical investigation. Acc Chem Res 50:2799–2808
156. Vautravers NR, Regent DD, Breit B (2011) Inter- and intramolecular hydroacylation of alkenes
employing a bifunctional catalyst system. Chem Commun 47:6635–6637
157. Tan G, Zhu L, Liao X, Lan Y, You J (2017) Rhodium/copper cocatalyzed highly trans-selective
1,2-diheteroarylation of alkynes with azoles via c-h addition/oxidative cross-coupling: a
combined experimental and theoretical study. J Am Chem Soc 139:15724–15737
1 Theoretical View of Rh-Catalyzed C–H Functionalization
137. Wodrich MD, Ye B, Gonthier JF, Corminboeuf C, Cramer N (2014) Ligand-controlled regiodivergent pathways of rhodium(III)-catalyzed dihydroisoquinolone synthesis: experimental and
computational studies of different cyclopentadienyl ligands. Chem A Eur J 20:15409–15418
138. Wu JQ, Zhang SS, Gao H, Qi Z, Zhou CJ, Ji WW, Liu Y, Chen Y, Li Q, Li X, Wang H
(2017) Experimental and theoretical studies on rhodium-catalyzed coupling of benzamides
with 2,2-Difluorovinyl tosylate: diverse synthesis of fluorinated heterocycles. J Am Chem
Soc 139:3537–3545
139. Yang YF, Houk KN, Wu YD (2016) Computational exploration of Rh(III)/Rh(V)
and Rh(III)/Rh(I) catalysis in Rhodium(III)-Catalyzed C–H activation reactions of NPhenoxyacetamides with alkynes. J Am Chem Soc 138:6861–6868
140. Yu S, Liu S, Lan Y, Wan B, Li X (2015) Rhodium-catalyzed C–H activation of phenacyl
ammonium salts assisted by an oxidizing C–N bond: a combination of experimental and
theoretical studies. J Am Chem Soc 137:1623–1631
141. Garcia-Cuadrado D, Braga AA, Maseras F, Echavarren AM (2006) Proton abstraction mechanism for the palladium-catalyzed intramolecular arylation. J Am Chem Soc 128:1066–1067
142. Lafrance M, Rowley CN, Woo TK, Fagnou K (2006) Catalytic intermolecular direct arylation
of perfluorobenzenes. J Am Chem Soc 128:8754–8756
143. Hoyano JK, Graham WAG (1982) Oxidative addition of the carbon-hydrogen bonds of neopentane and cyclohexane to a photochemically generated iridium(I) complex. J Am Chem Soc
104:3723–3725
144. Pivsa-Art S, Satoh T, Kawamura Y, Miura M, Nomura M (1998) Palladium-catalyzed arylation
of azole compounds with aryl halides in the presence of alkali metal carbonates and the use
of copper iodide in the reaction. Bull Chem Soc Japan 71:467–473
145. Watson PL (1983) Methane exchange reactions of lanthanide and early-transition-metal
methyl complexes. J Am Chem Soc 105:6491–6493
146. Guan ZH, Ren ZH, Spinella SM, Yu S, Liang YM, Zhang X (2009) Rhodium-catalyzed
direct oxidative carbonylation of aromatic C–H bond with CO and alcohols. J Am Chem Soc
131:729–733
147. Ishii Y, Chatani N, Kakiuchi F, Murai S (1997) Rhodium-catalyzed reaction of N-(2Pyridinyl)piperazines with CO and ethylene. a novel carbonylation at a C − H bond in the
piperazine ring. Organometallics 16:3615–3622
148. Deng H, Li H, Wang L (2015) A unique alkylation of azobenzenes with allyl acetates by
Rh(III)-Catalyzed C–H functionalization. Org Lett 17:2450–2453
149. Huang L, Wang Q, Qi J, Wu X, Huang K, Jiang H (2013) Rh(iii)-catalyzed ortho-oxidative
alkylation of unactivated arenes with allylic alcohols. Chem Sci 4:2665
150. Shibata K, Chatani N (2014) Rhodium-catalyzed alkylation of C-H bonds in aromatic amides
with alpha, beta-unsaturated esters. Org Lett 16:5148–5151
151. Dateer RB, Chang S (2015) Selective cyclization of arylnitrones to indolines under external
oxidant-free conditions: dual role of Rh(III) catalyst in the C–H activation and oxygen atom
transfer. J Am Chem Soc 137:4908–4911
152. Sharma U, Park Y, Chang S (2014) Rh(III)-catalyzed traceless coupling of quinoline N-oxides
with internal diarylalkynes. J Org Chem 79:9899–9906
153. Chen X, Zheng G, Li Y, Song G, Li X (2017) Rhodium-catalyzed site-selective coupling of
indoles with diazo esters: C4-alkylation versus C2-Annulation. Org Lett 19:6184–6187
154. Wu Y, Chen Z, Yang Y, Zhu W, Zhou B (2018) Rh(III)-catalyzed redox-neutral unsymmetrical
c–h alkylation and amidation reactions of N-Phenoxyacetamides. J Am Chem Soc 140:42–45
155. Qi X, Li Y, Bai R, Lan Y (2017) Mechanism of rhodium-catalyzed C–H functionalization:
advances in theoretical investigation. Acc Chem Res 50:2799–2808
156. Vautravers NR, Regent DD, Breit B (2011) Inter- and intramolecular hydroacylation of alkenes
employing a bifunctional catalyst system. Chem Commun 47:6635–6637
157. Tan G, Zhu L, Liao X, Lan Y, You J (2017) Rhodium/copper cocatalyzed highly trans-selective
1,2-diheteroarylation of alkynes with azoles via c-h addition/oxidative cross-coupling: a
combined experimental and theoretical study. J Am Chem Soc 139:15724–15737