Crossed intermolecular [2+2] cycloaddition of styrenes by visible light photocatalysis

被引:158
作者
Ischay, Michael A. [1 ]
Ament, Michael S. [1 ]
Yoon, Tehshik P. [1 ]
机构
[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
关键词
PHOTOREDOX CATALYSIS; PHOTOCHEMISTRY; CYCLOREVERSION; DIMERIZATION; COMPLEXES; STRATEGY;
D O I
10.1039/c2sc20658g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report a method for the crossed [2 + 2] cycloaddition of styrenes using visible light photocatalysis. Few methods for the synthesis of unsymmetrically substituted cyclobutanes by photochemical [2 + 2] cycloaddition are known. We show that careful tuning of the electrochemical properties of a ruthenium photocatalyst enable the efficient crossed [2 + 2] cycloaddition of styrenes upon irradiation with visible light. We outline the logic that enables high crossed chemoselectivity, and we also demonstrate that this reaction is remarkably efficient; gram-scale reactions can be conducted with as little as 0.025 mol% of the photocatalyst.
引用
收藏
页码:2807 / 2811
页数:5
相关论文
共 47 条
[1]   Photochemical Reactions as Key Steps in Natural Product Synthesis [J].
Bach, Thorsten ;
Hehn, Joerg P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) :1000-1045
[2]   A STRATEGY FOR INTERMOLECULAR DIELS-ALDER CYCLO-ADDITION TO ENAMIDES [J].
BAULD, NL ;
HARIRCHIAN, B ;
REYNOLDS, DW ;
WHITE, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (24) :8111-8117
[3]   CATION RADICAL CATALYZED OLEFIN CYCLO-DIMERIZATION [J].
BAULD, NL ;
PABON, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (03) :633-634
[4]   CATION RADICAL CYCLO-ADDITIONS AND RELATED SIGMATROPIC REACTIONS [J].
BAULD, NL .
TETRAHEDRON, 1989, 45 (17) :5307-5363
[5]   THEORY OF CATION-RADICAL PERICYCLIC-REACTIONS [J].
BAULD, NL ;
BELLVILLE, DJ ;
PABON, R ;
CHELSKY, R ;
GREEN, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (08) :2378-2382
[6]   CYCLODIMERIZATION OF STYRENE [J].
BROWN, WG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (07) :1916-&
[7]   PHOTOCHEMISTRY OF THE PHENANTHRENE-STILBENE SYSTEM - CYCLOADDITION AND SINGLET-SENSITIZED ISOMERIZATION [J].
CALDWELL, RA ;
MIZUNO, K ;
HANSEN, PE ;
VO, IP ;
FRENTRUP, M ;
HO, CD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (24) :7263-7269
[8]   PHOTOCHEMICAL 2+2 CYCLOADDITION VIA A CATION-RADICAL CHAIN REACTION [J].
CRELLIN, RA ;
LAMBERT, MC ;
LEDWITH, A .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1970, (11) :682-&
[9]   SYNTHETIC APPLICATIONS OF INTRAMOLECULAR ENONE OLEFIN PHOTOCYCLOADDITIONS [J].
CRIMMINS, MT .
CHEMICAL REVIEWS, 1988, 88 (08) :1453-1473
[10]   RUTHENIUM(II) TRIS(BIPYRAZYL) DICATION - A NEW PHOTOCATALYST [J].
CRUTCHLEY, RJ ;
LEVER, ABP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (23) :7128-7129