Highly Satisfactory Procedures for the Pd-Catalyzed Cross Coupling of Aryl Electrophiles with in Situ Generated Alkynylzinc Derivatives

Abstract

[reaction: see text] Two new and very efficient procedures (Procedures A and B) are reported for the Pd-catalyzed cross coupling of aryl electrophiles with terminal alkynes via their in situ conversion into alkynylzinc derivatives. Procedure A is particularly valuable in cases where electron-deficient alkynes are used, while Procedure B is operationally simple and very satisfactory in less demanding cases.

Highly Efficient Pd/Tetraphosphine Catalytic System for Copper-Free Sonogashira Reactions of Aryl Bromides with Terminal Alkynes

“…Meanwhile, Hierso et al [13] reported a [BMIM] [BF 4 ]-[Pd(C 3 H 5 )Cl] 2 -dppf system for the coupling of aryl bromides under copper-free condition. Additives (silver or zinc salts) were alternative choice to promote the reaction but might cause the catalytic system more complicated [14][15][16][17]. Herein simple copper-free protocols without those salts were published later.…”

Quantitative Structure–Retention Relationships for Polycyclic Aromatic Hydrocarbons and their Oligoalkynyl‐Substituted Derivatives

“…Samples of 2b, [47,48] 2e, [49][50][51] 1c, [52] 1d, [52,53] 2c, [54] 2d, [54] 3c, [55,56] 3d, [55,56] and 4c [57] were prepared by following the approach as shown for the alkynyl-substituted anthracenes (Scheme 1, Supporting Information). Thus, the ethynyl-substituted anthracenes 2b and 2e were obtained by aN egishi-type coupling [58][59][60][61] of 9-bromoanthracene or 9,10-dibromoanthracene with ethynyltrimethylsilane (Scheme 1, step a) following ap rocedure by John and To ur. [62] Subsequent protodesilylation by using K 2 CO 3 in methanol provided the free terminal acetylenes (Scheme 1, step b).…”

New Method for Synthesis of 3-Arylindolizines from Electron-Deficient Alkynes through 1, 3-Dipolar Cycloaddition

“…在此基础上, 我们发展了一种以缺电子 炔烃为原料经 1,3-偶极环加成反应合成 3-芳基中氮茚的 新方法. [13] , 4e [14] , 4f [14] , 4g [15] 按文献方法合成. [12] , 5b [12] , 5c [12] , 5i [10c] , 5n [8] , 5p [16] 为已知化合物, 其核磁氢谱与文献报道一致.…”