Recent advances of carbonyl olefination via McMurry coupling reaction

Abstract

McMurry coupling reaction utilizes the low-valent titanium reagents and carbonyl compounds to produce olefins.

Electroreductive alkylations of (hetero)arenes with carboxylic acids

“…In addition, high-resolution mass analysis of the hydrogenative coupling of benzoic acid with anisole suggested the involvement of a titanium carbene intermediate 72 in this transformation 63 , and a tetrasubstituted alkene 73 by McMurry reaction was also observed as a minor product (Fig. 4d ) 64 – 66 . Moreover, the kinetic isotope effect experiments were performed using deuterated and non-deuterated reagents (Fig.…”

Electroreductive alkylations of (hetero)arenes with carboxylic acids

“…In addition, high-resolution mass analysis of the hydrogenative coupling of benzoic acid with anisole suggested the involvement of a titanium carbene intermediate 72 in this transformation 63 , and a tetrasubstituted alkene 73 by McMurry reaction was also observed as a minor product (Fig. 4d ) 64 – 66 . Moreover, the kinetic isotope effect experiments were performed using deuterated and non-deuterated reagents (Fig.…”

Regioselective π‐Extension of Helical PAHs: Tuning Energy Gaps and Excited‐State Dynamics Directed by Clar's Sextet Migration

“…For the synthesis of 1 , 4,5,6,7,8,9-hexahydroperylene-2carbaldehyde ( 3 ) was prepared from α-tetralone in five steps with an overall yield of 18% (Scheme S1 ). Subsequent McMurry coupling [ 33,34 ] followed by Mallory photocyclization-using iodine as oxidant and propylene oxide as an acid scavenger [ 35,36 ]-afforded the key intermediate, 4,5,6,7,12,13,14,15-tetrakis-(propan-1,3-diyl) [7]helicene ( 5 ) in 12%. The moderate yield is likely attributable to the formation of regioisomers during the non-selective photocyclization step from 4 to 5 .…”

Photo-Triggerable Polymerization and Depolymerization of Stiff-Stilbene Lactones

“…The monomers were prepared from readily available precursors, and the final cyclization was achieved via the McMurry reaction ( Figure a and Supporting Information Scheme S1 for full synthetic protocols). The resulting monomers, M1 4 – M6 11 (superscripted number refers to the number of atoms in the linker), were fully characterized with 1 H NMR, 13 C NMR and mass spectrometry. Notably, the structures of M3 8 and M6 11 were confirmed by single-crystal X-ray diffraction (SC-XRD, Figure d).…”

Electroreductive alkylations of (hetero)arenes with carboxylic acids

“…In addition, high-resolution mass analysis of the hydrogenative coupling of benzoic acid with anisole suggested the involvement of a titanium carbene intermediate 72 in this transformation 63 , and a tetrasubstituted alkene 73 by McMurry reaction was also observed as a minor product (Fig. 4d ) 64 – 66 . Moreover, the kinetic isotope effect experiments were performed using deuterated and non-deuterated reagents (Fig.…”

Regioselective π‐Extension of Helical PAHs: Tuning Energy Gaps and Excited‐State Dynamics Directed by Clar's Sextet Migration

“…For the synthesis of 1 , 4,5,6,7,8,9-hexahydroperylene-2carbaldehyde ( 3 ) was prepared from α-tetralone in five steps with an overall yield of 18% (Scheme S1 ). Subsequent McMurry coupling [ 33,34 ] followed by Mallory photocyclization-using iodine as oxidant and propylene oxide as an acid scavenger [ 35,36 ]-afforded the key intermediate, 4,5,6,7,12,13,14,15-tetrakis-(propan-1,3-diyl) [7]helicene ( 5 ) in 12%. The moderate yield is likely attributable to the formation of regioisomers during the non-selective photocyclization step from 4 to 5 .…”

Photo-Triggerable Polymerization and Depolymerization of Stiff-Stilbene Lactones

“…The monomers were prepared from readily available precursors, and the final cyclization was achieved via the McMurry reaction ( Figure a and Supporting Information Scheme S1 for full synthetic protocols). The resulting monomers, M1 4 – M6 11 (superscripted number refers to the number of atoms in the linker), were fully characterized with 1 H NMR, 13 C NMR and mass spectrometry. Notably, the structures of M3 8 and M6 11 were confirmed by single-crystal X-ray diffraction (SC-XRD, Figure d).…”

Electroreductive alkylations of (hetero)arenes with carboxylic acids

“…In addition, high-resolution mass analysis of the hydrogenative coupling of benzoic acid with anisole suggested the involvement of a titanium carbene intermediate 72 in this transformation 63 , and a tetrasubstituted alkene 73 by McMurry reaction was also observed as a minor product (Fig. 4d ) 64 – 66 . Moreover, the kinetic isotope effect experiments were performed using deuterated and non-deuterated reagents (Fig.…”

Regioselective π‐Extension of Helical PAHs: Tuning Energy Gaps and Excited‐State Dynamics Directed by Clar's Sextet Migration

“…For the synthesis of 1 , 4,5,6,7,8,9-hexahydroperylene-2carbaldehyde ( 3 ) was prepared from α-tetralone in five steps with an overall yield of 18% (Scheme S1 ). Subsequent McMurry coupling [ 33,34 ] followed by Mallory photocyclization-using iodine as oxidant and propylene oxide as an acid scavenger [ 35,36 ]-afforded the key intermediate, 4,5,6,7,12,13,14,15-tetrakis-(propan-1,3-diyl) [7]helicene ( 5 ) in 12%. The moderate yield is likely attributable to the formation of regioisomers during the non-selective photocyclization step from 4 to 5 .…”

Photo-Triggerable Polymerization and Depolymerization of Stiff-Stilbene Lactones

“…The monomers were prepared from readily available precursors, and the final cyclization was achieved via the McMurry reaction ( Figure a and Supporting Information Scheme S1 for full synthetic protocols). The resulting monomers, M1 4 – M6 11 (superscripted number refers to the number of atoms in the linker), were fully characterized with 1 H NMR, 13 C NMR and mass spectrometry. Notably, the structures of M3 8 and M6 11 were confirmed by single-crystal X-ray diffraction (SC-XRD, Figure d).…”