Bulky yet Flexible Alkyl Substituents at Remote Positions in Tertiary Phosphines: Synthesis and Catalytic Performance of the Phosphine Ligands in the Nickel-Catalyzed Suzuki–Miyaura Reaction

The structural design of tertiary alkylphosphines is extremely important for controlling the activity of homogeneous metal catalysts. However, inexpensive monodentate phosphines that can exhibit high catalytic performance are limited. Recently, tertiary phosphines bearing bulky aryl substituents at remote positions have been reported as ligands for efficient cross-coupling reactions. In this study, we found that a primary alkyl group having two remote <i>tert</i>-butyl groups can be introduced into the phosphorus atom by using readily available materials. As expected, the new phosphine ligands exhibited high catalytic performance in nickel-catalyzed Suzuki-Miyaura cross coupling.

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Journal
Organic Letters
Published
2025-11-08
DOI
https://doi.org/10.1021/acs.orglett.5c04126
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
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article

Bulky yet Flexible Alkyl Substituents at Remote Positions in Tertiary Phosphines: Synthesis and Catalytic Performance of the Phosphine Ligands in the Nickel-Catalyzed Suzuki–Miyaura Reaction

T. Sato, Yoshio Shibasaki, Tsutomu Takashima, Kouki Matsubara et al.
Organic Letters
Catalytic Cross-Coupling Reactions
article

Bulky yet Flexible Alkyl Substituents at Remote Positions in Tertiary Phosphines: Synthesis and Catalytic Performance of the Phosphine Ligands in the Nickel-Catalyzed Suzuki–Miyaura Reaction

T. Sato, Yoshio Shibasaki, Tsutomu Takashima, Kouki Matsubara, Yoshihiro Asai, Yukiya Hakozaki, Yuji Koga, Kanako Miyoshi, Yuichiro Tago, Manato Moriguchi
article en

Abstract

The structural design of tertiary alkylphosphines is extremely important for controlling the activity of homogeneous metal catalysts. However, inexpensive monodentate phosphines that can exhibit high catalytic performance are limited. Recently, tertiary phosphines bearing bulky aryl substituents at remote positions have been reported as ligands for efficient cross-coupling reactions. In this study, we found that a primary alkyl group having two remote <i>tert</i>-butyl groups can be introduced into the phosphorus atom by using readily available materials. As expected, the new phosphine ligands exhibited high catalytic performance in nickel-catalyzed Suzuki-Miyaura cross coupling.

Organic LettersVol. 27(49)
Fukuoka University (JP), Eneos (Japan) (JP)
Openalex Percentile: Top 75%
Catalytic Cross-Coupling Reactions
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Bulky yet Flexible Alkyl Substituents at Remote Positions in Tertiary Phosphines: Synthesis and Catalytic Performance of the Phosphine Ligands in the Nickel-Catalyzed Suzuki–Miyaura Reaction — T. Sato, Yoshio Shibasaki, et al. · Organic Letters (2025) | TGRS Research Map | TGRS