The Application of Pulse Radiolysis to the Study of Ni(I) Intermediates in Ni-Catalyzed Cross-Coupling Reactions

被引：78

作者：

Till, Nicholas A. ^{[1
]}

Oh, Seokjoon ^{[2
]}

MacMillan, David W. C. ^{[1
]}

Bird, Matthew J. ^{[2
]}

机构：

[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA

[2] Brookhaven Natl Lab, Chem Div, Upton, NY 11973 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2021年 / 143卷 / 25期

关键词：

PHOTOREDOX; TRANSIENT; METAL;

D O I：

10.1021/jacs.1c04652

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Here we report the use of pulse radiolysis and spectroelectrochemistry to generate low-valent nickel intermediates relevant to synthetically important Ni-catalyzed cross-coupling reactions and interrogate their reactivities toward comproportio-nation and oxidative addition processes. Pulse radiolysis provided a direct means to generate singly reduced [(dtbbpy)NiBr], enabling the identification of a rapid Ni(0)/Ni(II) comproportionation process taking place under synthetically relevant electrolysis conditions. This approach also permitted the direct measurement of Ni(I) oxidative addition rates with electronically differentiated aryl iodide electrophiles (k(OA) = 1.3 x 10(4)-2.4 x 10(5) M-1 s(-1)), an elementary organometallic step often proposed in nickel-catalyzed cross-coupling reactions. Together, these results hold implications for a number of Ni-catalyzed cross-coupling processes.

引用

页码：9332 / 9337

页数：6

共 46 条

[1] ABSOLUTE DETERMINATION OF ELECTRON CONSUMPTION IN TRANSIENT OR STEADY-STATE ELECTROCHEMICAL TECHNIQUES [J].

AMATORE, C ;

AZZABI, M ;

CALAS, P ;

JUTAND, A ;

LEFROU, C ;

ROLLIN, Y .

JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1990, 288 (1-2) :45-63

[2] The photophysics of photoredox catalysis: a roadmap for catalyst design [J].

Arias-Rotondo, Daniela M. ;

McCusker, James K. .

CHEMICAL SOCIETY REVIEWS, 2016, 45 (21) :5803-5820

[3] Synthesis and Reactivity of Paramagnetic Nickel Polypyridyl Complexes Relevant to C(sp2)-C(sp3)Coupling Reactions [J].

Beromi, Megan Mohadjer ;

Brudvig, Gary W. ;

Hazari, Nilay ;

Lant, Hannah M. C. ;

Mercado, Brandon Q. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (18) :6094-6098

[4] Mechanism and Selectivity in Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Halides with Alkyl Halides [J].

Biswas, Soumik ;

Weix, Daniel J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (43) :16192-16197

[5] Exploring Mechanisms in Ni Terpyridine Catalyzed C-C Cross-Coupling Reactions-A Review [J].

Budnikova, Yulia H. ;

Vicic, David A. ;

Klein, Axel .

INORGANICS, 2018, 6 (01)

[6] Redox Trends in Terpyridine Nickel Complexes [J].

Ciszewski, James T. ;

Mikhaylov, Dmitry Y. ;

Holin, Kirill V. ;

Kadirov, Marsil K. ;

Budnikova, Yulia H. ;

Sinyashin, Oleg ;

Vicic, David A. .

INORGANIC CHEMISTRY, 2011, 50 (17) :8630-8635

[7] Mechanisms of Nickel-Catalyzed Cross-Coupling Reactions [J].

Diccianni, Justin B. ;

Diao, Tianning .

TRENDS IN CHEMISTRY, 2019, 1 (09) :830-844

[8] Expanding the Medicinal Chemist Toolbox: Comparing Seven C(sp2)-C(sp3) Cross-Coupling Methods by Library Synthesis [J].

Dombrowski, Amanda W. ;

Gesmundo, Nathan J. ;

Aguirre, Ana L. ;

Sarris, Katerina A. ;

Young, Jonathon M. ;

Bogdan, Andrew R. ;

Martin, M. Cynthia ;

Gedeon, Shasline ;

Wang, Ying .

ACS MEDICINAL CHEMISTRY LETTERS, 2020, 11 (04) :597-604

[9] Overcoming limitations in dual photoredox/nickel-catalysed C-N cross-couplings due to catalyst deactivation [J].

Gisbertz, Sebastian ;

Reischauer, Susanne ;

Pieber, Bartholomaeus .

NATURE CATALYSIS, 2020, 3 (08) :611-620

[10] Application of Pulse Radiolysis to Mechanistic Investigations of Catalysis Relevant to Artificial Photosynthesis [J].

Grills, David C. ;

Polyansky, Dmitry E. ;

Fujita, Etsuko .

CHEMSUSCHEM, 2017, 10 (22) :4359-4373

← 1 2 3 4 5 →