Chelate Silylene–Silyl Ligand Can Boost Rhodium‐Catalyzed C−H Bond Functionalization Reactions
The first N‐heterocyclic silylene (NHSi)–silane scaffold LSi−R−Si(H)Mes2 (1) (L=PhC(NtBu)2; R=1,12‐xanthendiyl spacer; Mes=2,4,6‐Me3C6H2) was synthesized and used to form the unique rhodium(III) complex (LSi−R−SiMes2)Rh(H)Cl 2 through its reaction with 0.5 molar equivalents of [Rh(coe)2Cl]2 (coe=cyc...
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| Published in | Chemistry : a European journal Vol. 24; no. 55; pp. 14608 - 14612 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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WEINHEIM
Wiley
01.10.2018
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| Abstract | The first N‐heterocyclic silylene (NHSi)–silane scaffold LSi−R−Si(H)Mes2 (1) (L=PhC(NtBu)2; R=1,12‐xanthendiyl spacer; Mes=2,4,6‐Me3C6H2) was synthesized and used to form the unique rhodium(III) complex (LSi−R−SiMes2)Rh(H)Cl 2 through its reaction with 0.5 molar equivalents of [Rh(coe)2Cl]2 (coe=cyclooctene). An X‐ray diffraction analysis revealed that 2 has a (SiIISiIV)Rh(H)Cl core with three short Rh⋅⋅⋅H−C contacts with Me groups of the ligand 1, which cause a distorted pentagonal bipyramidal coordination of the Rh center. Unexpectedly, the reaction of 2 with tBuONa gives the new bis(silyl)hydridorhodium(III) complex 4. Due to the strong donor ability of the chelate SiII–SiIV ligand, 2 and 4 can act as highly efficient pre‐catalysts in the Rh‐mediated selective C−H functionalization of 2‐phenylpyridines with C−C unsaturated organic substrates under mild reaction conditions.
Agostic complexes: A pentagonal‐bipyramidal rhodium(III) complex featuring one agostic and two anagostic interactions with a new SiII–SiIV ligand has been synthesized. It can be used as pre‐catalyst for alkenylation and alkylation of C−H bonds with high catalytic efficiency under mild reaction conditions (see scheme). |
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| AbstractList | The first N‐heterocyclic silylene (NHSi)–silane scaffold LSi−R−Si(H)Mes
2
(
1
) (L=PhC(N
t
Bu)
2
; R=1,12‐xanthendiyl spacer; Mes=2,4,6‐Me
3
C
6
H
2
) was synthesized and used to form the unique rhodium(III) complex (LSi−R−SiMes
2
)Rh(H)Cl
2
through its reaction with 0.5 molar equivalents of [Rh(coe)
2
Cl]
2
(coe=cyclooctene). An X‐ray diffraction analysis revealed that
2
has a (Si
II
Si
IV
)Rh(H)Cl core with three short Rh
⋅⋅⋅
H−C contacts with Me groups of the ligand
1
, which cause a distorted pentagonal bipyramidal coordination of the Rh center. Unexpectedly, the reaction of
2
with
t
BuONa gives the new bis(silyl)hydridorhodium(III) complex
4
. Due to the strong donor ability of the chelate Si
II
–Si
IV
ligand,
2
and
4
can act as highly efficient pre‐catalysts in the Rh‐mediated selective C−H functionalization of 2‐phenylpyridines with C−C unsaturated organic substrates under mild reaction conditions. The first N-heterocyclic silylene (NHSi)-silane scaffold LSi-R-Si(H)Mes(2) (1) (L = PhC(NtBu)(2); R = 1,12-xanthendiyl spacer; Mes = 2,4,6-Me3C6H2) was synthesized and used to form the unique rhodium(III) complex (LSi-R-SiMes(2))Rh(H)Cl 2 through its reaction with 0.5 molar equivalents of [Rh(coe)(2)Cl](2) (coe=cyclooctene). An X-ray diffraction analysis revealed that 2 has a ((SiSiIV)-Si-II)Rh(H)Cl core with three short Rh center dot center dot center dot H-C contacts with Me groups of the ligand 1, which cause a distorted pentagonal bipyramidal coordination of the Rh center. Unexpectedly, the reaction of 2 with tBuONa gives the new bis(silyl)hydridorhodium(III) complex 4. Due to the strong donor ability of the chelate Si-II-Si-IV ligand, 2 and 4 can act as highly efficient pre-catalysts in the Rh-mediated selective C-H functionalization of 2-phenylpyridines with C-C unsaturated organic substrates under mild reaction conditions. The first N‐heterocyclic silylene (NHSi)–silane scaffold LSi−R−Si(H)Mes2 (1) (L=PhC(NtBu)2; R=1,12‐xanthendiyl spacer; Mes=2,4,6‐Me3C6H2) was synthesized and used to form the unique rhodium(III) complex (LSi−R−SiMes2)Rh(H)Cl 2 through its reaction with 0.5 molar equivalents of [Rh(coe)2Cl]2 (coe=cyclooctene). An X‐ray diffraction analysis revealed that 2 has a (SiIISiIV)Rh(H)Cl core with three short Rh⋅⋅⋅H−C contacts with Me groups of the ligand 1, which cause a distorted pentagonal bipyramidal coordination of the Rh center. Unexpectedly, the reaction of 2 with tBuONa gives the new bis(silyl)hydridorhodium(III) complex 4. Due to the strong donor ability of the chelate SiII–SiIV ligand, 2 and 4 can act as highly efficient pre‐catalysts in the Rh‐mediated selective C−H functionalization of 2‐phenylpyridines with C−C unsaturated organic substrates under mild reaction conditions. Agostic complexes: A pentagonal‐bipyramidal rhodium(III) complex featuring one agostic and two anagostic interactions with a new SiII–SiIV ligand has been synthesized. It can be used as pre‐catalyst for alkenylation and alkylation of C−H bonds with high catalytic efficiency under mild reaction conditions (see scheme). The first N-heterocyclic silylene (NHSi)-silane scaffold LSi-R-Si(H)Mes2 (1) (L=PhC(NtBu)2 ; R=1,12-xanthendiyl spacer; Mes=2,4,6-Me3 C6 H2 ) was synthesized and used to form the unique rhodium(III) complex (LSi-R-SiMes2 )Rh(H)Cl 2 through its reaction with 0.5 molar equivalents of [Rh(coe)2 Cl]2 (coe=cyclooctene). An X-ray diffraction analysis revealed that 2 has a (SiII SiIV )Rh(H)Cl core with three short Rh⋅⋅⋅H-C contacts with Me groups of the ligand 1, which cause a distorted pentagonal bipyramidal coordination of the Rh center. Unexpectedly, the reaction of 2 with tBuONa gives the new bis(silyl)hydridorhodium(III) complex 4. Due to the strong donor ability of the chelate SiII -SiIV ligand, 2 and 4 can act as highly efficient pre-catalysts in the Rh-mediated selective C-H functionalization of 2-phenylpyridines with C-C unsaturated organic substrates under mild reaction conditions.The first N-heterocyclic silylene (NHSi)-silane scaffold LSi-R-Si(H)Mes2 (1) (L=PhC(NtBu)2 ; R=1,12-xanthendiyl spacer; Mes=2,4,6-Me3 C6 H2 ) was synthesized and used to form the unique rhodium(III) complex (LSi-R-SiMes2 )Rh(H)Cl 2 through its reaction with 0.5 molar equivalents of [Rh(coe)2 Cl]2 (coe=cyclooctene). An X-ray diffraction analysis revealed that 2 has a (SiII SiIV )Rh(H)Cl core with three short Rh⋅⋅⋅H-C contacts with Me groups of the ligand 1, which cause a distorted pentagonal bipyramidal coordination of the Rh center. Unexpectedly, the reaction of 2 with tBuONa gives the new bis(silyl)hydridorhodium(III) complex 4. Due to the strong donor ability of the chelate SiII -SiIV ligand, 2 and 4 can act as highly efficient pre-catalysts in the Rh-mediated selective C-H functionalization of 2-phenylpyridines with C-C unsaturated organic substrates under mild reaction conditions. The first N‐heterocyclic silylene (NHSi)–silane scaffold LSi−R−Si(H)Mes2 (1) (L=PhC(NtBu)2; R=1,12‐xanthendiyl spacer; Mes=2,4,6‐Me3C6H2) was synthesized and used to form the unique rhodium(III) complex (LSi−R−SiMes2)Rh(H)Cl 2 through its reaction with 0.5 molar equivalents of [Rh(coe)2Cl]2 (coe=cyclooctene). An X‐ray diffraction analysis revealed that 2 has a (SiIISiIV)Rh(H)Cl core with three short Rh⋅⋅⋅H−C contacts with Me groups of the ligand 1, which cause a distorted pentagonal bipyramidal coordination of the Rh center. Unexpectedly, the reaction of 2 with tBuONa gives the new bis(silyl)hydridorhodium(III) complex 4. Due to the strong donor ability of the chelate SiII–SiIV ligand, 2 and 4 can act as highly efficient pre‐catalysts in the Rh‐mediated selective C−H functionalization of 2‐phenylpyridines with C−C unsaturated organic substrates under mild reaction conditions. |
| Author | Mo, Zhenbo Yao, Shenglai Driess, Matthias Zhou, Yu‐Peng Kostenko, Arseni |
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| Keywords | ALKANE COMPLEXES ACTIVATION (9,9-DIMETHYLXANTHENE-4,5-DIYL)BIS(DIMETHYLSILYL) AGOSTIC INTERACTIONS N-heterocyclic silylenes N-H RUTHENIUM(II) COMPLEX CARBON-HYDROGEN BONDS agostic complexes MOLECULES alkenylation density functional calculations atoms in molecules INTERMEDIATE METAL-COMPLEXES |
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| Snippet | The first N‐heterocyclic silylene (NHSi)–silane scaffold LSi−R−Si(H)Mes2 (1) (L=PhC(NtBu)2; R=1,12‐xanthendiyl spacer; Mes=2,4,6‐Me3C6H2) was synthesized and... The first N‐heterocyclic silylene (NHSi)–silane scaffold LSi−R−Si(H)Mes 2 ( 1 ) (L=PhC(N t Bu) 2 ; R=1,12‐xanthendiyl spacer; Mes=2,4,6‐Me 3 C 6 H 2 ) was... The first N-heterocyclic silylene (NHSi)-silane scaffold LSi-R-Si(H)Mes(2) (1) (L = PhC(NtBu)(2); R = 1,12-xanthendiyl spacer; Mes = 2,4,6-Me3C6H2) was... The first N-heterocyclic silylene (NHSi)-silane scaffold LSi-R-Si(H)Mes2 (1) (L=PhC(NtBu)2 ; R=1,12-xanthendiyl spacer; Mes=2,4,6-Me3 C6 H2 ) was synthesized... |
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| SubjectTerms | agostic complexes alkenylation atoms in molecules Catalysts Chelates Chemical reactions Chemistry Chemistry, Multidisciplinary density functional calculations Ligands N-heterocyclic silylenes Physical Sciences Rhodium Science & Technology Substrates X-ray diffraction |
| Title | Chelate Silylene–Silyl Ligand Can Boost Rhodium‐Catalyzed C−H Bond Functionalization Reactions |
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