Radical cascade reactions triggered by single electron transfer

被引:244
作者
Plesniak, Mateusz P. [1 ]
Huang, Huan-Ming [1 ]
Procter, David J. [1 ]
机构
[1] Univ Manchester, Sch Chem, Oxford Rd, Manchester M13 9PL, Lancs, England
基金
英国工程与自然科学研究理事会;
关键词
COPPER-CATALYZED TRIFLUOROMETHYLATION; CONCISE TOTAL-SYNTHESIS; LEWIS-ACID CATALYSIS; CYCLIZATION CASCADES; TRANSITION-METAL; PHOTOREDOX CATALYSIS; BOND FORMATION; DIASTEREOSELECTIVE SYNTHESIS; OXIDATIVE DECARBOXYLATION; STRAIGHTFORWARD SYNTHESIS;
D O I
10.1038/s41570-017-0077
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The rapid generation of molecular complexity from simple starting materials is of paramount importance in synthetic chemistry. The unique combination of high reactivity and high selectivity often associated with open-shell intermediates makes radical chemistry ideal for cascade reactions, in which simple substrates undergo a series of processes involving bond formation (and bond cleavage) to give complex, high-value products. Crucially, radical cascade reactions can greatly diminish the time, cost and amount of waste associated with complex target synthesis. Recent exciting advances in the field of radical chemistry initiated by single electron transfer (SET) have led to a considerable upward shift in our ability to design powerful new cascade reactions. This Review highlights recent advances in the development of radical cascades, triggered by SET processes, that deliver molecular constructs of importance in medicine and biology.
引用
收藏
页数:16
相关论文
共 144 条
[1]   Enantioselective Photocatalytic [3+2] Cycloadditions of Aryl Cyclopropyl Ketones [J].
Amador, Adrian G. ;
Sherbrook, Evan M. ;
Yoon, Tehshik P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (14) :4722-4725
[2]   SILVER(I)-CATALYZED OXIDATIVE DECARBOXYLATION OF ACIDS BY PEROXYDISULFATE - ROLE OF SILVER(II) [J].
ANDERSON, JM ;
KOCHI, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (06) :1651-&
[3]   Cascade polycyclizations in natural product synthesis [J].
Ardkhean, R. ;
Caputo, D. F. J. ;
Morrow, S. M. ;
Shi, H. ;
Xiong, Y. ;
Anderson, E. A. .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (06) :1557-1569
[4]  
Baralle A., 2012, ENCYCLOPEDIA OF RADI
[5]   KOtBu: A Privileged Reagent for Electron Transfer Reactions? [J].
Barham, Joshua P. ;
Coulthard, Graeme ;
Emery, Katie J. ;
Doni, Eswararao ;
Cumine, Florimond ;
Nocera, Giuseppe ;
John, Matthew P. ;
Berlouis, Leonard E. A. ;
McGuire, Thomas ;
Tuttle, Tell ;
Murphy, John A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (23) :7402-7410
[6]   A new strategy for the synthesis of cyclic terpenoids based on the radical opening of acyclic epoxypolyenes [J].
Barrero, AF ;
Cuerva, JM ;
Herrador, MM ;
Valdivia, MV .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (11) :4074-4078
[7]   PYRROLIDINES BY INTRAMOLECULAR ADDITION OF KOLBE RADICALS GENERATED FROM BETA-ALLYLAMINOALKANOATES [J].
BECKING, L ;
SCHAFER, HJ .
TETRAHEDRON LETTERS, 1988, 29 (23) :2797-2800
[8]   Samarium diiodide induced ketyl-(het)arene cyclisations towards novel N-heterocycles [J].
Beemelmanns, Christine ;
Reissig, Hans-Ulrich .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (05) :2199-2210
[9]   A Short Formal Total Synthesis of Strychnine with a Samarium Diiodide Induced Cascade Reaction as the Key Step [J].
Beemelmanns, Christine ;
Reissig, Hans-Ulrich .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (43) :8021-8025
[10]   Total Synthesis of (+)-Crotogoudin [J].
Breitler, Simon ;
Carreira, Erick M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (42) :11168-11171