Evolution and Synthetic Applications of the Heck-Matsuda Reaction: The Return of Arenediazonium Salts to Prominence

被引:268
作者
Taylor, Jason G. [1 ]
Moro, Angelica Venturini [1 ]
Correia, Carlos Roque D. [1 ]
机构
[1] Univ Estadual Campinas, UNICAMP, Inst Quim, BR-13084971 Campinas, SP, Brazil
基金
巴西圣保罗研究基金会;
关键词
Arenediazonium salts; Palladium; Heck reaction; Arylation; Alkenes; REDUCTION-CYCLIZATION HRC; PALLADIUM-CATALYZED HYDROARYLATION; CROSS-COUPLING REACTIONS; DIAZONIUM SALTS; TRANSITION-METALS; ARYLDIAZONIUM SALTS; MIZOROKI-HECK; STEREOSELECTIVE-SYNTHESIS; TETRAFLUOROBORATE SALTS; ROOM-TEMPERATURE;
D O I
10.1002/ejoc.201001620
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This review highlights the potential and the versatility of arenediazonium salts as viable alternatives to conventional aryl halides and oxygen-based electrophiles for Pd-catalyzed Heck reactions. It also presents an overview of the field over the last decade, including some historical perspective of the Heck-Matsuda (HM) reaction with general considerations regarding reaction conditions, type of catalysts used, and the application of arenediazonium salts as reagents for the HM arylation of several types of alkenes. Throughout this review, the principal aspects related to reactivity and selectivity are discussed, and when applicable a comparison is made between the HM and the conventional Heck reactions. One-pot procedures that involve generation of the arenediazonium salt in situ from the corresponding aniline have been presented as well as some useful heterogeneous catalytic protocols. Allylic alcohols, conjugated alkenes, unsaturated heterocycles, and unactivated alkenes are capable of being arylated with arenediazonium salts by using simple catalysts such as Pd(OAc)(2) or Pd-2(dba)(3) at room temperature in air and in benign and conventional solvents. In addition to the intramolecular variant of the HM reaction, intermolecular tandem coupling-cyclization processes have also been developed for the construction of a range of oxygen and nitrogen heterocycles. Finally, several applications towards the total synthesis of biologically active natural and nonnatural compounds are highlighted as well as the use of the HM reaction in the synthesis of new chiral, nonracemic ligands.
引用
收藏
页码:1403 / 1428
页数:26
相关论文
共 135 条
[71]   REACTION OF DIAZONIUM SALTS WITH TRANSITION-METALS .8. PALLADIUM-CATALYZED CARBON CARBON COUPLING OF ARENEDIAZONIUM SALTS WITH ORGANOTIN COMPOUNDS [J].
KIKUKAWA, K ;
KONO, K ;
WADA, F ;
MATSUDA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (08) :1333-1336
[72]   REACTION OF DIAZONIUM SALTS WITH TRANSITION-METALS .9. REACTION OF VINYLTRIMETHYLSILANE WITH ARENEDIAZONIUM TETRAFLUOROBORATES UNDER PALLADIUM(O) CATALYSIS [J].
KIKUKAWA, K ;
IKENAGA, K ;
KONO, K ;
TORITANI, K ;
WADA, F ;
MATSUDA, T .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1984, 270 (03) :277-282
[73]   ARYLATION OF OLEFINS BY N-NITROSO-N-ARYLACETAMIDES UNDER PALLADIUM(0) CATALYSIS - A NEW PRECURSOR OF ARYLPALLADIUM SPECIES [J].
KIKUKAWA, K ;
NARITOMI, M ;
HE, GX ;
WADA, F ;
MATSUDA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (03) :299-301
[74]   Supported palladium catalysts in Heck coupling reactions -: Problems, potential and recent advances [J].
Koehler, K. ;
Proeckl, S. S. ;
Kleist, W. .
CURRENT ORGANIC CHEMISTRY, 2006, 10 (13) :1585-1601
[75]   A novel synthesis of trifluoromethylated multi-substituted alkenes via regio- and stereoselective Heck reaction of (E)-4,4,4-trifluoro-1-phenyl-2-buten-1-one [J].
Konno, Tsutomu ;
Yamada, Shigeyuki ;
Tani, Akinori ;
Miyabe, Tomotsugu ;
Ishibara, Takashi .
SYNLETT, 2006, (18) :3025-3028
[76]   Unexpected high regiocontrol in Heck reaction of fluorine-containing electron-deficient olefins-Highly regio- and stereoselective synthesis of β-fluoroalkyl-α-aryl-α,β-unsaturated ketones [J].
Konno, Tsutomu ;
Yamada, Shigeyuki ;
Tani, Akinori ;
Nishida, Masataka ;
Miyabe, Tomotsugu ;
Ishihara, Takashi .
JOURNAL OF FLUORINE CHEMISTRY, 2009, 130 (10) :913-921
[77]   PALLADIUM-MEDIATED COUPLING OF A 3-DEOXY PYRANOID GLYCAL - STEREOCHEMISTRY OF C-GLYCOSYL BOND FORMATION [J].
KWOK, DI ;
FARR, RN ;
DAVES, GD .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (11) :3711-3713
[78]   A Multi-Task Palladium Catalyst Involved in Heck-Reduction-Cyclization Sequences for the Preparation of 4-Benzyl-1,2-dihydroisoquinolin-3-ones: An Unusual Homogeneous-Heterogeneous Sustainable Approach [J].
Laudien, Julia ;
Fouquet, Eric ;
Zakri, Cecile ;
Felpin, Francois-Xavier .
SYNLETT, 2010, (10) :1539-1543
[79]   The scope of the Heck arylation of enol ethers with arenediazonium salts: a new approach to the syntheses of flavonoids [J].
Machado, Angelo H. L. ;
de Sousa, Marcio A. ;
Patto, Daniela C. S. ;
Azevedo, Luis F. S. ;
Bombonato, Fernando I. ;
Correia, Carlos Roque D. .
TETRAHEDRON LETTERS, 2009, 50 (11) :1222-1225
[80]   The Heck-type arylation of allylic alcohols with arenediazonium salts [J].
Masllorens, J ;
Bouquillon, S ;
Roglans, A ;
Hénin, F ;
Muzart, J .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (16) :3822-3826