Cobaloxime-Catalyzed Hydrogen Evolution in Photoredox-Facilitated Small-Molecule Functionalization

被引：62

作者：

Cartwright, Kaitie C. ^{[1
]}

Davies, Alex M. ^{[1
]}

Tunge, Jon A. ^{[1
]}

机构：

[1] Univ Kansas, Dept Chem, 1567 Irving Hill Rd, Lawrence, KS 66045 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 10期

基金：

美国国家科学基金会;

关键词：

Dehydrogenation; Hydrogen evolution; Photocatalysis; Photoredox catalysis; Synthesic methods; ACCEPTORLESS DEHYDROGENATION; ARTIFICIAL PHOTOSYNTHESIS; HOMOGENEOUS SYSTEM; H-2; EVOLUTION; H BOND; C-C; COBALT; WATER; COMPLEXES; ACTIVATION;

D O I：

10.1002/ejoc.201901170

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The development of efficient, mild, economical, and low-waste processes is a cornerstone of sustainable chemistry. One such synthetic strategy that exemplifies these characteristics is the use of catalytic dehydrogenation in small-molecule functionalization. This has been achieved in recent history through the use of photoredox catalysis in conjunction with cobaloximes, a class of catalysts that are capable of proton reduction. This has allowed for a variety of bond formations to be achieved with few to no stoichiometric additives while often producing hydrogen gas as the sole stoichiometric by-product. Herein, select advancements made in this area of sustainable chemistry and catalysis are detailed and the mechanistic insights this body of work has provided thus far are evaluated. As such, this review aims to aid in the further development and study of synthetic strategies involving photoredox-promoted hydrogen evolution.

引用

页码：1245 / 1258

页数：14

共 115 条

[51] Making Hydrogen from Water Using a Homogeneous System Without Noble Metals [J].

Lazarides, Theodore ;

McCormick, Theresa ;

Du, Pingwu ;

Luo, Gengeng ;

Lindley, Brian ;

Eisenberg, Richard .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (26) :9192-+

[52] Powering the planet: Chemical challenges in solar energy utilization [J].

Lewis, Nathan S. ;

Nocera, Daniel G. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (50) :20142-20142

[53] Green chemistry for chemical synthesis [J].

Li, Chao-Jun ;

Trost, Barry M. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2008, 105 (36) :13197-13202

[54] Cross-Dehydrogenative Coupling (CDC): Exploring C-C Bond Formations beyond Functional Group Transformations [J].

Li, Chao-Jun .

ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (02) :335-344

[55] Evidence for Formation of a Co-H Bond from (H2O)2Co(dmgBF2)2 under H2: Application to Radical Cyclizations [J].

Li, Gang ;

Han, Arthur ;

Pulling, Mary E. ;

Estes, Deven P. ;

Norton, Jack R. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (36) :14662-14665

[56] Theoretical studies of the mechanism of catalytic hydrogen production by a cobaloxime [J].

Muckerman, James T. ;

Fujita, Etsuko .

CHEMICAL COMMUNICATIONS, 2011, 47 (46) :12456-12458

[57] Supramolecular Cobaloxime Assemblies for H2 Photocatalysis An Initial Solution State Structure-Function Analysis [J].

Mulfort, Karen L. ;

Tiede, David M. .

JOURNAL OF PHYSICAL CHEMISTRY B, 2010, 114 (45) :14572-14581

[58] Visible light photoredox catalysis: applications in organic synthesis [J].

Narayanam, Jagan M. R. ;

Stephenson, Corey R. J. .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (01) :102-113

[59] Elucidating the Key Role of pH on Light-Driven Hydrogen Evolution by a Molecular Cobalt Catalyst [J].

Natali, Mirco .

ACS CATALYSIS, 2017, 7 (02) :1330-1339

[60] Metal-Free, Cooperative Asymmetric Organophotoredox Catalysis with Visible Light [J].

Neumann, Matthias ;

Fueldner, Stefan ;

Koenig, Burkhard ;

Zeitler, Kirsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (04) :951-954

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