A Practical and General Diels-Alder Reaction of Pentafulvenes with Arynes

被引:52
作者
Bhojgude, Sachin Suresh [1 ]
Kaicharla, Trinadh [1 ]
Bhunia, Anup [1 ]
Biju, Akkattu T. [1 ]
机构
[1] CSIR NCL, Div Organ Chem, Pune 411008, Maharashtra, India
关键词
1,3-DIPOLAR CYCLOADDITION; ORGANIC-SYNTHESIS; CARBON-CARBON; SIGMA-BONDS; FULVENES; CHEMISTRY; BENZYNE; DERIVATIVES; EFFICIENT; BENZONORBORNADIENES;
D O I
10.1021/ol301742k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A high-yielding, versatile and practical Diels-Alder reaction of pentafulvenes with arynes under mild reaction conditions is reported. The aryne generated by the fluoride induced 1,2-elimination of 2-(trimethylsilyl)aryl triflates undergoes efficient cycloaddition with 6-substituted and 6,6-disubstituted pentafulvenes leading to the formation of benzonorbornadiene derivatives.
引用
收藏
页码:4098 / 4101
页数:4
相关论文
共 51 条
[1]   GENERATION OF 2,3-BENZOBICYCLO[2.2.1]HEPT-2-ENE-5,7-DIYL DIRADICALS VIA DENITROGENATION OF APPROPRIATE AZOALKANES AND THEIR MECHANISTIC IMPLICATIONS IN THE DI-PI-METHANE REARRANGEMENT OF BENZONORBORNADIENES [J].
ADAM, W ;
DELUCCHI, O .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (21) :4133-4138
[2]   CYCLO-ADDITION OF 4-PHENYL-4H-1,2,4-TRIAZOLE-3,5-DIONE (PTAD) TO 7-ALKYLIDENE-2,3-BENZONORBORNADIENES [J].
ADAM, W ;
LUCCHINI, V ;
PETERS, EM ;
PETERS, K ;
PASQUATO, L ;
VONSCHNERING, HG ;
SEGUCHI, K ;
WALTER, H ;
WILL, B .
CHEMISCHE BERICHTE, 1989, 122 (01) :133-143
[3]   BICYCLIC AZOALKANES VIA URAZOLES DERIVED FROM CYCLOADDITION OF "N-PHENYL-1,2,4-TRIAZOLINE-3,5-DIONE WITH STRAINED BICYCLOALKENES [J].
ADAM, W ;
DELUCCHI, O ;
ERDEN, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (14) :4806-4809
[4]  
ALPER H, 1980, SYNTHESIS-STUTTGART, P799
[5]   FULVENES AND SUBSTITUTED FULVENES [J].
BERGMANN, ED .
CHEMICAL REVIEWS, 1968, 68 (01) :41-&
[6]   Arynes in Transition-Metal-Free Multicomponent Coupling Reactions [J].
Bhojgude, Sachin Suresh ;
Biju, Akkattu T. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (07) :1520-1522
[7]   Recent advances in transition-metal-free carbon-carbon and carbon-heteroatom bond-forming reactions using arynes [J].
Bhunia, Anup ;
Yetra, Santhivardhana Reddy ;
Biju, Akkattu T. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (08) :3140-3152
[8]   NUCLEOPHILIC-SUBSTITUTION IN 5,6,7,8-TETRAFLUORO-1,4-METHANONAHTHALENES AND 6,7-DIFLUORO-1,2,3,4-TETRAHYDRO-9-ALKENYL-1,4-METHANONAPHTHALENES AND RELATED COMPOUNDS - SEARCH FOR HOMOALLYLIC CONJUGATION [J].
BROOKE, GM ;
YOUNG, AC .
JOURNAL OF FLUORINE CHEMISTRY, 1976, 8 (03) :223-241
[9]   Indole-derived arynes and their diels-alder reactivity with Furans [J].
Buszek, Keith R. ;
Luo, Diheng ;
Kondrashov, Mikhail ;
Brown, Nell ;
VanderVelde, David .
ORGANIC LETTERS, 2007, 9 (21) :4135-4137
[10]  
Chen Y, 2009, MODERN ARYLATION METHODS, P401, DOI 10.1002/9783527627325.ch12