"cationic" Suzuki-Miyaura Coupling with Acutely Base-Sensitive Boronic Acids

Liye Chen; Daniel R. Sanchez; Bufan Zhang; Brad P. Carrow

doi:10.1021/jacs.7b07687

"cationic" Suzuki-Miyaura Coupling with Acutely Base-Sensitive Boronic Acids

Liye Chen, Daniel R. Sanchez, Bufan Zhang, Brad P. Carrow

Chemistry

Research output: Contribution to journal › Article › peer-review

83 Scopus citations

Abstract

Fast, base-promoted protodeboronation of polyfluoroaryl and heteroaryl boronic acids complicates their use in Suzuki-Miyaura coupling (SMC) because a base is generally required for catalysis. We report a "cationic" SMC method using a PAd₃-Pd catalyst that proceeds at rt in the absence of a base or metal mediator. A wide range of sensitive boronic acids, particularly polyfluoroaryl substrates that are poorly compatible with classic SMC conditions, undergo clean coupling. Stoichiometric experiments implicate the intermediacy of organopalladium cations, which supports a long-postulated cationic pathway for transmetalation in SMC.

Original language	English (US)
Pages (from-to)	12418-12421
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	36
DOIs	https://doi.org/10.1021/jacs.7b07687
State	Published - Sep 13 2017

All Science Journal Classification (ASJC) codes

General Chemistry
Biochemistry
Catalysis
Colloid and Surface Chemistry

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10.1021/jacs.7b07687

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abstract = "Fast, base-promoted protodeboronation of polyfluoroaryl and heteroaryl boronic acids complicates their use in Suzuki-Miyaura coupling (SMC) because a base is generally required for catalysis. We report a {"}cationic{"} SMC method using a PAd3-Pd catalyst that proceeds at rt in the absence of a base or metal mediator. A wide range of sensitive boronic acids, particularly polyfluoroaryl substrates that are poorly compatible with classic SMC conditions, undergo clean coupling. Stoichiometric experiments implicate the intermediacy of organopalladium cations, which supports a long-postulated cationic pathway for transmetalation in SMC.",

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AU - Chen, Liye

AU - Sanchez, Daniel R.

AU - Zhang, Bufan

AU - Carrow, Brad P.

PY - 2017/9/13

Y1 - 2017/9/13

N2 - Fast, base-promoted protodeboronation of polyfluoroaryl and heteroaryl boronic acids complicates their use in Suzuki-Miyaura coupling (SMC) because a base is generally required for catalysis. We report a "cationic" SMC method using a PAd3-Pd catalyst that proceeds at rt in the absence of a base or metal mediator. A wide range of sensitive boronic acids, particularly polyfluoroaryl substrates that are poorly compatible with classic SMC conditions, undergo clean coupling. Stoichiometric experiments implicate the intermediacy of organopalladium cations, which supports a long-postulated cationic pathway for transmetalation in SMC.

AB - Fast, base-promoted protodeboronation of polyfluoroaryl and heteroaryl boronic acids complicates their use in Suzuki-Miyaura coupling (SMC) because a base is generally required for catalysis. We report a "cationic" SMC method using a PAd3-Pd catalyst that proceeds at rt in the absence of a base or metal mediator. A wide range of sensitive boronic acids, particularly polyfluoroaryl substrates that are poorly compatible with classic SMC conditions, undergo clean coupling. Stoichiometric experiments implicate the intermediacy of organopalladium cations, which supports a long-postulated cationic pathway for transmetalation in SMC.

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"cationic" Suzuki-Miyaura Coupling with Acutely Base-Sensitive Boronic Acids

Abstract

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