Palladium-Catalyzed Dehydrogenative Coupling Reaction of Terminal Alkynes with Unactivated Alkenes

被引：6

作者：

Yada, Akira ^{[1
]}

Nishi, Shoki ^{[2
]}

Sato, Yuta ^{[2
]}

Ichinoseki, Sakina ^{[1
]}

Murakami, Masahiro ^{[2
]}

机构：

[1] Natl Inst Adv Ind Sci & Technol, Interdisciplinary Res Ctr Catalyt Chem, 1-1-1 Higashi, Tsukuba, Ibaraki 3058565, Japan

[2] Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan

来源：

JOURNAL OF THE CHINESE CHEMICAL SOCIETY | 2018年 / 65卷 / 01期

关键词：

Dehydrogenative coupling; Palladium; 1,3-Enyne; Terminal alkyne; Alkene; ACCESS; ALKYNYLATION; DERIVATIVES; 1,3-ENYNES; EPOXIDES; ENYNES;

D O I：

10.1002/jccs.201700268

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Terminal alkynes having a bulky substituent dehydrogenatively couple with unactivated terminal alkenes with catalysis of palladium. The terminal sp carbon forms a bond with the internal sp(2) carbon of the alkene regioselectively to produce branched, conjugated 1,3-enynes with wide functional group tolerance.

引用

页码：117 / 121

页数：5

共 35 条

[1] Regioselective Synthesis of 3-Hydroxy-4,5-alkyl-Substituted Pyridines Using 1,3-Enynes as Alkynes Surrogates [J].

Barday, Manuel ;

Ho, Kelvin Y. T. ;

Halsall, Christopher T. ;

Aissa, Christophe .

ORGANIC LETTERS, 2016, 18 (08) :1756-1759

[2] 1,10-PHENANTHROLINE DERIVATIVES - A NEW LIGAND CLASS IN THE HECK REACTION - MECHANISTIC ASPECTS [J].

CABRI, W ;

CANDIANI, I ;

BEDESCHI, A ;

SANTI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26) :7421-7426

[3] The sonogashira reaction:: A booming methodology in synthetic organic chemistry [J].

Chinchilla, Rafael ;

Najera, Carmen .

CHEMICAL REVIEWS, 2007, 107 (03) :874-922

[4] A highly selective synthesis of diarylethynes and their oligomers by a palladium-catalyzed Sonogashira coupling reaction under phase transfer conditions [J].

Chow, HF ;

Wan, CW ;

Low, KH ;

Yeung, YY .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (05) :1910-1913

[5] Small but effective:: Copper hydride catalyzed synthesis of α-hydroxyallenes [J].

Deutsch, Carl ;

Lipshutz, Bruce H. ;

Krause, Norbert .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1650-1653

[6] Regio- and stereoselective homocoupling of γ-arylated tert-propargyl alcohols with liberation of a ketone molecule and successive cyclization to produce fluorescent dihydrofuran derivatives [J].

Funayama, A ;

Satoh, T ;

Miura, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (44) :15354-15355

[7] Concise and practical synthesis of latrunculin A by ring-closing enyne-yne metathesis [J].

Fürstner, A ;

Turet, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (22) :3462-3466

[8] NEW ECOTOXICOLOGICALLY AND BIOGENETICALLY RELEVANT TERPENES OF THE TROPICAL GREEN SEAWEED CAULERPA-TAXIFOLIA WHICH IS INVADING THE MEDITERRANEAN [J].

GUERRIERO, A ;

MARCHETTI, F ;

DAMBROSIO, M ;

SENESI, S ;

DINI, F ;

PIETRA, F .

HELVETICA CHIMICA ACTA, 1993, 76 (02) :855-864

[9] Expeditious enyne construction from alkynes via oxidative Pd(II)-catalyzed Heck-type coupling [J].

Hadi, Victor ;

Yoo, Kyung Soo ;

Jeong, Min ;

Jung, Kyung Woon .

TETRAHEDRON LETTERS, 2009, 50 (20) :2370-2373

[10] The first direct coupling of 1-trialkylsilyl-1-alkynes with vinyl triflates; a new access to enynes [J].

Halbes, U ;

Bertus, P ;

Pale, P .

TETRAHEDRON LETTERS, 2001, 42 (49) :8641-8644

← 1 2 3 4 →