Reactivity of Frustrated Lewis Pair: Carbocation versus Radical Intermediates
Recent reports of radical formation within frustrated Lewis pairs (FLPs) suggested that single‐electron transfer (SET) could play an important role in their chemistry especially for C−C coupling. In sharp contrast, our extensive dispersion‐corrected DFT calculations show that although reactive benzh...
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| Published in | Chemistry : a European journal Vol. 30; no. 11; pp. e202303901 - n/a |
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| Abstract | Recent reports of radical formation within frustrated Lewis pairs (FLPs) suggested that single‐electron transfer (SET) could play an important role in their chemistry especially for C−C coupling. In sharp contrast, our extensive dispersion‐corrected DFT calculations show that although reactive benzhydryl radical along with phosphine radical cation species can be kinetically generated from bulky phosphines and benzhydryl cation, direct P−C hetero‐coupling may lead to bulky phosphonium cation as reactive carbocation transfer reagents to styrene substrates, which is kinetically much more favorable than the recently proposed radical C−C coupling between benzhydryl radical and styrene. Similarly, meta‐stable radical cation Mes3P+⋅ salt is also kinetically accessible via SET reactions of Mes3P and B(C6F5)3 with 0.5 equivalent of p‐O2C6Cl4.
Extensive DFT calculations show that both radical HCAr2⋅ and carbocation HCAr2+ are thermally accessible from the bulky phosphonium Mes3P−CHAr2+, which are further kinetically favored by HCAr2⋅ radical self‐dimerization and by nucleophilic alkene trapping, respectively. |
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| AbstractList | Recent reports of radical formation within frustrated Lewis pairs (FLPs) suggested that single-electron transfer (SET) could play an important role in their chemistry especially for C-C coupling. In sharp contrast, our extensive dispersion-corrected DFT calculations show that although reactive benzhydryl radical along with phosphine radical cation species can be kinetically generated from bulky phosphines and benzhydryl cation, direct P-C hetero-coupling may lead to bulky phosphonium cation as reactive carbocation transfer reagents to styrene substrates, which is kinetically much more favorable than the recently proposed radical C-C coupling between benzhydryl radical and styrene. Similarly, meta-stable radical cation Mes
P
⋅ salt is also kinetically accessible via SET reactions of Mes
P and B(C
F
)
with 0.5 equivalent of p-O
C
Cl
. Recent reports of radical formation within frustrated Lewis pairs (FLPs) suggested that single‐electron transfer (SET) could play an important role in their chemistry especially for C−C coupling. In sharp contrast, our extensive dispersion‐corrected DFT calculations show that although reactive benzhydryl radical along with phosphine radical cation species can be kinetically generated from bulky phosphines and benzhydryl cation, direct P−C hetero‐coupling may lead to bulky phosphonium cation as reactive carbocation transfer reagents to styrene substrates, which is kinetically much more favorable than the recently proposed radical C−C coupling between benzhydryl radical and styrene. Similarly, meta‐stable radical cation Mes3P+⋅ salt is also kinetically accessible via SET reactions of Mes3P and B(C6F5)3 with 0.5 equivalent of p‐O2C6Cl4. Recent reports of radical formation within frustrated Lewis pairs (FLPs) suggested that single‐electron transfer (SET) could play an important role in their chemistry especially for C−C coupling. In sharp contrast, our extensive dispersion‐corrected DFT calculations show that although reactive benzhydryl radical along with phosphine radical cation species can be kinetically generated from bulky phosphines and benzhydryl cation, direct P−C hetero‐coupling may lead to bulky phosphonium cation as reactive carbocation transfer reagents to styrene substrates, which is kinetically much more favorable than the recently proposed radical C−C coupling between benzhydryl radical and styrene. Similarly, meta‐stable radical cation Mes 3 P + ⋅ salt is also kinetically accessible via SET reactions of Mes 3 P and B(C 6 F 5 ) 3 with 0.5 equivalent of p ‐O 2 C 6 Cl 4 . Recent reports of radical formation within frustrated Lewis pairs (FLPs) suggested that single‐electron transfer (SET) could play an important role in their chemistry especially for C−C coupling. In sharp contrast, our extensive dispersion‐corrected DFT calculations show that although reactive benzhydryl radical along with phosphine radical cation species can be kinetically generated from bulky phosphines and benzhydryl cation, direct P−C hetero‐coupling may lead to bulky phosphonium cation as reactive carbocation transfer reagents to styrene substrates, which is kinetically much more favorable than the recently proposed radical C−C coupling between benzhydryl radical and styrene. Similarly, meta‐stable radical cation Mes3P+⋅ salt is also kinetically accessible via SET reactions of Mes3P and B(C6F5)3 with 0.5 equivalent of p‐O2C6Cl4. Extensive DFT calculations show that both radical HCAr2⋅ and carbocation HCAr2+ are thermally accessible from the bulky phosphonium Mes3P−CHAr2+, which are further kinetically favored by HCAr2⋅ radical self‐dimerization and by nucleophilic alkene trapping, respectively. Recent reports of radical formation within frustrated Lewis pairs (FLPs) suggested that single-electron transfer (SET) could play an important role in their chemistry especially for C-C coupling. In sharp contrast, our extensive dispersion-corrected DFT calculations show that although reactive benzhydryl radical along with phosphine radical cation species can be kinetically generated from bulky phosphines and benzhydryl cation, direct P-C hetero-coupling may lead to bulky phosphonium cation as reactive carbocation transfer reagents to styrene substrates, which is kinetically much more favorable than the recently proposed radical C-C coupling between benzhydryl radical and styrene. Similarly, meta-stable radical cation Mes3 P+ ⋅ salt is also kinetically accessible via SET reactions of Mes3 P and B(C6 F5 )3 with 0.5 equivalent of p-O2 C6 Cl4 .Recent reports of radical formation within frustrated Lewis pairs (FLPs) suggested that single-electron transfer (SET) could play an important role in their chemistry especially for C-C coupling. In sharp contrast, our extensive dispersion-corrected DFT calculations show that although reactive benzhydryl radical along with phosphine radical cation species can be kinetically generated from bulky phosphines and benzhydryl cation, direct P-C hetero-coupling may lead to bulky phosphonium cation as reactive carbocation transfer reagents to styrene substrates, which is kinetically much more favorable than the recently proposed radical C-C coupling between benzhydryl radical and styrene. Similarly, meta-stable radical cation Mes3 P+ ⋅ salt is also kinetically accessible via SET reactions of Mes3 P and B(C6 F5 )3 with 0.5 equivalent of p-O2 C6 Cl4 . |
| Author | Qu, Zheng‐Wang Zhu, Hui Grimme, Stefan |
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| Snippet | Recent reports of radical formation within frustrated Lewis pairs (FLPs) suggested that single‐electron transfer (SET) could play an important role in their... Recent reports of radical formation within frustrated Lewis pairs (FLPs) suggested that single-electron transfer (SET) could play an important role in their... |
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| SubjectTerms | carbocation Cations Coupling DFT calculations Electron transfer FLP Intermediates Phosphine Phosphines radical reaction mechanism Reagents Styrene Styrenes Substrates |
| Title | Reactivity of Frustrated Lewis Pair: Carbocation versus Radical Intermediates |
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