Ruthenium(II)-Catalyzed Regioselective C-H Arylation of Cyclic and N,N-Dialkyl Benzamides with Boronic Acids by Weak Coordination

Pradeep Nareddy; Frank Jordan; Stacey E. Brenner-Moyer; Michal Szostak

doi:https://doi.org/10.1021/acscatal.6b01360

Ruthenium(II)-Catalyzed Regioselective C-H Arylation of Cyclic and N,N-Dialkyl Benzamides with Boronic Acids by Weak Coordination

Pradeep Nareddy, Frank Jordan, Stacey E. Brenner-Moyer, Michal Szostak

Rutgers, The State University

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

66 Scopus citations

Abstract

We disclose a general method for selective ortho-C-H arylation of cyclic and N,N-dialkyl benzamides with boronic acids enabled by versatile ruthenium(II) complexes. This method features a general C-H arylation of ubiquitous aromatic tertiary benzamides by weak O-coordination. The transformation is characterized by its operational simplicity, the use of inexpensive, air-stable Ru(II) catalysts, scalability, and wide substrate scope. The reaction proceeds with high monoarylation selectivity to furnish valuable tertiary amide biaryls. Most crucially, the method provides the long-sought alternative to the classic directed-ortho-metalation (DoM) strategy, obviating the need for cryogenic conditions and strong lithium bases.

Original language	American English
Pages (from-to)	4755-4759
Number of pages	5
Journal	ACS Catalysis
Volume	6
Issue number	7
DOIs	https://doi.org/10.1021/acscatal.6b01360
State	Published - Jul 1 2016

ASJC Scopus subject areas

Catalysis
Chemistry(all)

Keywords

C-H activation
amides
boronic acids
directed-ortho-metalation
ruthenium

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https://doi.org/10.1021/acscatal.6b01360

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title = "Ruthenium(II)-Catalyzed Regioselective C-H Arylation of Cyclic and N,N-Dialkyl Benzamides with Boronic Acids by Weak Coordination",

abstract = "We disclose a general method for selective ortho-C-H arylation of cyclic and N,N-dialkyl benzamides with boronic acids enabled by versatile ruthenium(II) complexes. This method features a general C-H arylation of ubiquitous aromatic tertiary benzamides by weak O-coordination. The transformation is characterized by its operational simplicity, the use of inexpensive, air-stable Ru(II) catalysts, scalability, and wide substrate scope. The reaction proceeds with high monoarylation selectivity to furnish valuable tertiary amide biaryls. Most crucially, the method provides the long-sought alternative to the classic directed-ortho-metalation (DoM) strategy, obviating the need for cryogenic conditions and strong lithium bases.",

keywords = "C-H activation, amides, boronic acids, directed-ortho-metalation, ruthenium",

author = "Pradeep Nareddy and Frank Jordan and Brenner-Moyer, {Stacey E.} and Michal Szostak",

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T1 - Ruthenium(II)-Catalyzed Regioselective C-H Arylation of Cyclic and N,N-Dialkyl Benzamides with Boronic Acids by Weak Coordination

AU - Nareddy, Pradeep

AU - Jordan, Frank

AU - Brenner-Moyer, Stacey E.

AU - Szostak, Michal

PY - 2016/7/1

Y1 - 2016/7/1

N2 - We disclose a general method for selective ortho-C-H arylation of cyclic and N,N-dialkyl benzamides with boronic acids enabled by versatile ruthenium(II) complexes. This method features a general C-H arylation of ubiquitous aromatic tertiary benzamides by weak O-coordination. The transformation is characterized by its operational simplicity, the use of inexpensive, air-stable Ru(II) catalysts, scalability, and wide substrate scope. The reaction proceeds with high monoarylation selectivity to furnish valuable tertiary amide biaryls. Most crucially, the method provides the long-sought alternative to the classic directed-ortho-metalation (DoM) strategy, obviating the need for cryogenic conditions and strong lithium bases.

AB - We disclose a general method for selective ortho-C-H arylation of cyclic and N,N-dialkyl benzamides with boronic acids enabled by versatile ruthenium(II) complexes. This method features a general C-H arylation of ubiquitous aromatic tertiary benzamides by weak O-coordination. The transformation is characterized by its operational simplicity, the use of inexpensive, air-stable Ru(II) catalysts, scalability, and wide substrate scope. The reaction proceeds with high monoarylation selectivity to furnish valuable tertiary amide biaryls. Most crucially, the method provides the long-sought alternative to the classic directed-ortho-metalation (DoM) strategy, obviating the need for cryogenic conditions and strong lithium bases.

KW - C-H activation

KW - amides

KW - boronic acids

KW - directed-ortho-metalation

KW - ruthenium

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Ruthenium(II)-Catalyzed Regioselective C-H Arylation of Cyclic and N,N-Dialkyl Benzamides with Boronic Acids by Weak Coordination

Abstract

ASJC Scopus subject areas

Keywords

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