94
3 Theoretical Study of Rh-Catalyzed …
171. Zhang J, Xie H, Zhu H, Zhang S, Reddy Lonka M, Zou H (2019) Chameleon-like behavior
of the directing group in the Rh(III)-catalyzed regioselective C–H amidation of indole: an
experimental and computational study. ACS Catal 9:10233–10244
172. Guimond N, Gorelsky SI, Fagnou K (2011) Rhodium(III)-catalyzed heterocycle synthesis
using an internal oxidant: improved reactivity and mechanistic studies. J Am Chem Soc
133:6449–6457
173. Xu L, Zhu Q, Huang G, Cheng B, Xia Y (2012) Computational elucidation of the internal
oxidant-controlled reaction pathways in Rh(III)-catalyzed aromatic C–H functionalization. J
Org Chem 77:3017–3024
174. Neufeldt SR, Jimenez-Oses G, Huckins JR, Thiel OR, Houk KN (2015) Pyridine n-oxide vs
pyridine substrates for Rh(III)-catalyzed oxidative C–H bond functionalization. J Am Chem
Soc 137:9843–9854
175. Huckins JR, Bercot EA, Thiel OR, Hwang T-L, Bio MM (2013) Rh(III)-catalyzed C–H activation and double directing group strategy for the regioselective synthesis of naphthyridinones.
J Am Chem Soc 135:14492–14495
176. Wu W, Liu Y, Bi S (2015) Mechanistic insight into conjugated N–N bond cleavage by Rh(III)catalyzed redox-neutral C–H activation of pyrazolones. Org Biomol Chem 13:8251–8260
177. Chen W-J, Lin Z (2015) Rhodium(III)-catalyzed hydrazine-directed C–H activation for indole
synthesis: mechanism and role of internal oxidant probed by DFT studies. Organometallics
34:309–318
178. Zhao D, Shi Z, Glorius F (2013) Indole synthesis by rhodium(III)-catalyzed hydrazinedirected C–H activation: redox-neutral and traceless by N–N bond cleavage. Angew Chem
Int Ed 52:12426–12429
179. Wang Q, Li Y, Qi Z, Xie F, Lan Y, Li X (2016) Rhodium(III)-catalyzed annulation between
N-sulfinyl ketoimines and activated olefins: C–H activation assisted by an oxidizing N–S
bond. ACS Catal 6:1971–1980
180. Chen X-Y, Gao Z-H, Ye S (2020) Bifunctional n-heterocyclic carbenes derived from LPyroglutamic acid and their applications in enantioselective organocatalysis. Acc Chem Res
53:690–702
181. Chen XY, Li S, Vetica F, Kumar M, Enders D (2018) N-heterocyclic-carbene-catalyzed
domino reactions via two or more activation modes. IScience 2:1–26
182. Jeletic MS, Ghiviriga I, Abboud KA, Veige AS (2007) Mono- and bimetallic rhodium(I)
complexes supported by newc-symmetric bis-n-heterocyclic carbene ligands: metalation via
C = C bond cleavage under Mild Conditions. Organometallics 26:5267–5270
183. Nair V, Rajesh C, Vinod AU, Bindu S, Sreekanth AR, Mathen JS, Balagopal L (2003) Strategies for heterocyclic construction via novel multicomponent reactions based on isocyanides
and nucleophilic carbenes. Acc Chem Res 36:899–907
184. Frenking G, Solà M, Vyboishchikov SF (2005) Chemical bonding in transition metal carbene
complexes. J Org Chem 690:6178–6204
185. Sierra MA (2000) Di- and polymetallic heteroatom stabilized (Fischer) metal carbene
complexes. Chem Rev 100:3591–3638
186. Velazquez HD, Verpoort F (2012) N-Heterocyclic carbene transition metal complexes for
catalysis in aqueous media. Chem Soc Rev 41:7032–7060
187. Xia Y, Zhang Y, Wang J (2013) Catalytic cascade reactions involving metal carbene migratory
insertion. ACS Catal 3:2586–2598
188. Chan WW, Lo SF, Zhou Z, Yu WY (2012) Rh-catalyzed intermolecular carbenoid functionalization of aromatic C–H bonds by alpha-diazomalonates. J Am Chem Soc 134:13565–13568
189. Lu Y-S, Yu W-Y (2016) Cp*Rh(III)-catalyzed cross-coupling of alkyltrifluoroborate with
alpha-diazomalonates for C(sp 3 )-C(sp 3 ) bond formation. Org Lett 18:1350–1353
190. Xia Y, Feng S, Liu Z, Zhang Y, Wang J (2015) Rhodium(I)-catalyzed sequential C(sp)-C(sp 3 )
and C(sp 3 )-C(sp 3 ) bond formation through migratory carbene insertion. Angew Chem Int Ed
54:7891–7894
191. Xia Y, Liu Z, Feng S, Ye F, Zhang Y, Wang J (2015) Rh(I)-catalyzed cross-coupling of
alpha-diazoesters with arylsiloxanes. Org Lett 17:956–959
3 Theoretical Study of Rh-Catalyzed …
171. Zhang J, Xie H, Zhu H, Zhang S, Reddy Lonka M, Zou H (2019) Chameleon-like behavior
of the directing group in the Rh(III)-catalyzed regioselective C–H amidation of indole: an
experimental and computational study. ACS Catal 9:10233–10244
172. Guimond N, Gorelsky SI, Fagnou K (2011) Rhodium(III)-catalyzed heterocycle synthesis
using an internal oxidant: improved reactivity and mechanistic studies. J Am Chem Soc
133:6449–6457
173. Xu L, Zhu Q, Huang G, Cheng B, Xia Y (2012) Computational elucidation of the internal
oxidant-controlled reaction pathways in Rh(III)-catalyzed aromatic C–H functionalization. J
Org Chem 77:3017–3024
174. Neufeldt SR, Jimenez-Oses G, Huckins JR, Thiel OR, Houk KN (2015) Pyridine n-oxide vs
pyridine substrates for Rh(III)-catalyzed oxidative C–H bond functionalization. J Am Chem
Soc 137:9843–9854
175. Huckins JR, Bercot EA, Thiel OR, Hwang T-L, Bio MM (2013) Rh(III)-catalyzed C–H activation and double directing group strategy for the regioselective synthesis of naphthyridinones.
J Am Chem Soc 135:14492–14495
176. Wu W, Liu Y, Bi S (2015) Mechanistic insight into conjugated N–N bond cleavage by Rh(III)catalyzed redox-neutral C–H activation of pyrazolones. Org Biomol Chem 13:8251–8260
177. Chen W-J, Lin Z (2015) Rhodium(III)-catalyzed hydrazine-directed C–H activation for indole
synthesis: mechanism and role of internal oxidant probed by DFT studies. Organometallics
34:309–318
178. Zhao D, Shi Z, Glorius F (2013) Indole synthesis by rhodium(III)-catalyzed hydrazinedirected C–H activation: redox-neutral and traceless by N–N bond cleavage. Angew Chem
Int Ed 52:12426–12429
179. Wang Q, Li Y, Qi Z, Xie F, Lan Y, Li X (2016) Rhodium(III)-catalyzed annulation between
N-sulfinyl ketoimines and activated olefins: C–H activation assisted by an oxidizing N–S
bond. ACS Catal 6:1971–1980
180. Chen X-Y, Gao Z-H, Ye S (2020) Bifunctional n-heterocyclic carbenes derived from LPyroglutamic acid and their applications in enantioselective organocatalysis. Acc Chem Res
53:690–702
181. Chen XY, Li S, Vetica F, Kumar M, Enders D (2018) N-heterocyclic-carbene-catalyzed
domino reactions via two or more activation modes. IScience 2:1–26
182. Jeletic MS, Ghiviriga I, Abboud KA, Veige AS (2007) Mono- and bimetallic rhodium(I)
complexes supported by newc-symmetric bis-n-heterocyclic carbene ligands: metalation via
C = C bond cleavage under Mild Conditions. Organometallics 26:5267–5270
183. Nair V, Rajesh C, Vinod AU, Bindu S, Sreekanth AR, Mathen JS, Balagopal L (2003) Strategies for heterocyclic construction via novel multicomponent reactions based on isocyanides
and nucleophilic carbenes. Acc Chem Res 36:899–907
184. Frenking G, Solà M, Vyboishchikov SF (2005) Chemical bonding in transition metal carbene
complexes. J Org Chem 690:6178–6204
185. Sierra MA (2000) Di- and polymetallic heteroatom stabilized (Fischer) metal carbene
complexes. Chem Rev 100:3591–3638
186. Velazquez HD, Verpoort F (2012) N-Heterocyclic carbene transition metal complexes for
catalysis in aqueous media. Chem Soc Rev 41:7032–7060
187. Xia Y, Zhang Y, Wang J (2013) Catalytic cascade reactions involving metal carbene migratory
insertion. ACS Catal 3:2586–2598
188. Chan WW, Lo SF, Zhou Z, Yu WY (2012) Rh-catalyzed intermolecular carbenoid functionalization of aromatic C–H bonds by alpha-diazomalonates. J Am Chem Soc 134:13565–13568
189. Lu Y-S, Yu W-Y (2016) Cp*Rh(III)-catalyzed cross-coupling of alkyltrifluoroborate with
alpha-diazomalonates for C(sp 3 )-C(sp 3 ) bond formation. Org Lett 18:1350–1353
190. Xia Y, Feng S, Liu Z, Zhang Y, Wang J (2015) Rhodium(I)-catalyzed sequential C(sp)-C(sp 3 )
and C(sp 3 )-C(sp 3 ) bond formation through migratory carbene insertion. Angew Chem Int Ed
54:7891–7894
191. Xia Y, Liu Z, Feng S, Ye F, Zhang Y, Wang J (2015) Rh(I)-catalyzed cross-coupling of
alpha-diazoesters with arylsiloxanes. Org Lett 17:956–959