Cycloadditions, cycloisomerizations and related reactions of alkynes bearing group 13 or 14 heteroelements

被引:60
作者
Gandon, V [1 ]
Aubert, C [1 ]
Malacria, M [1 ]
机构
[1] Univ Paris 06, CNRS, Lab Chim Organ Assoc, F-75252 Paris, France
关键词
D O I
10.2174/138527205774610895
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cycloaddition and cycloisomerization reactions involving alkynes grant a rapid access to arenes, cyclic dienes, and cyclopentenone derivatives. The use of alkynes substituted by group 13 or 14 heteroelements as partners for such reactions is an emerging strategy. Indeed, the specific electronic properties of these heteroelements can play a crucial role for controlling the chemo- and regioselective outcome of a given reaction. Moreover, the heteroatoms can be considered as latent functional groups and would allow for further transformations including Suzuki-Miyaura or Stille cross-couplings. Both aspects will be presented in this review.
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页码:1699 / 1712
页数:14
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共 146 条
[11]   Synthesis of bent [4]phenylene (cyclobuta[1,2-α:3,4-b′]bisbiphenylene) and structure of a bis(trimethylsilyl) derivative:: the last [4] phenylene isomer [J].
Bong, DTY ;
Gentric, L ;
Holmes, D ;
Matzger, AJ ;
Scherhag, F ;
Vollhardt, KPC .
CHEMICAL COMMUNICATIONS, 2002, (03) :278-279
[12]   Molybdenum(III) chloride tetrahydrothiophene (tht) complexes in the catalytic polymerization and cyclotrimerization of alkynes: Structures and reactivities of the possible intermediates [MoCl3(tht)(2)(PhC CR)] (R=Me or Et) [J].
Boorman, PM ;
Wang, MP ;
Parvez, M .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1996, (24) :4533-4542
[13]  
BROOK MA, 2000, SILICON ORGAIC ORGAN
[14]   ALKYNE CYCLIZATIONS AT REDUCED TANTALUM CENTERS - SYNTHESIS AND MOLECULAR-STRUCTURE OF (ETA-6-C6ME6)TA(O-2,6-I-PR2C6H3)2CL [J].
BRUCK, MA ;
COPENHAVER, AS ;
WIGLEY, DE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (21) :6525-6527
[15]   The first total synthesis of 15-deoxy-Δ 12,14-prostaglandin J2 and the unambiguous assignment of the C14 stereochemistry [J].
Brummond, KM ;
Sill, PC ;
Chen, HF .
ORGANIC LETTERS, 2004, 6 (02) :149-152
[16]   The synthesis of a dicyclopenta[a,e]pentalene via a molybdenum hexacarbonyl-mediated tandem allenic Pauson-Khand reaction [J].
Cao, H ;
Flippen-Anderson, J ;
Cook, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (11) :3230-3231
[17]   METAL-MEDIATED [6+2]-CYCLOADDITIONS OF ALKYNES TO CYCLOHEPTATRIENE AND N-CARBETHOXYAZEPINE [J].
CHAFFEE, K ;
HUO, P ;
SHERIDAN, JB ;
BARBIERI, A ;
AISTARS, A ;
LALANCETTE, RA ;
OSTRANDER, RL ;
RHEINGOLD, AL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (07) :1900-1907
[18]   Ruthenium-catalyzed carbonylative cycloaddition of α-keto lactones with alkenes or alkynes:: The participation of an ester-carbonyl group in cycloaddition reactions as the two-atom assembling unit [J].
Chatani, N ;
Amako, K ;
Tobisu, M ;
Asaumi, T ;
Fukumoto, Y ;
Murai, S .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04) :1591-1593
[19]   Totally chemo- and regioselective cobalt(I)-mediated formal intermolecular cyclotrimerization of alkynes [J].
Chouraqui, G ;
Petit, M ;
Aubert, C ;
Malacria, M .
ORGANIC LETTERS, 2004, 6 (09) :1519-1521
[20]  
CIOLOWSKY J, 1993, J AM CHEM SOC, V115, P1353