Synthesis of stereoisomerically pube (E)-1,5-diyn-3-enes and (E)-1-bromo-3-yn-1-enes by diastereoselective palladium-catalyzed cross-coupling reaction of 1-alkynylzinc chlorides with a stereoisomeric mixture of 1,2-dibromoethylene.
Graphical Abstract
(E)-1,5-Diyn-3-enes and (E)-1-bromo-3-yn-l-enes have been stereoselectively synthesized starting from a diastereoisomeric mixture of 1,2-dibromoethylene.
References (8)
- et al.
- et al.
Tetrahedron Lett.
(1986)
Cited by (35)
Coupling Reactions Between C(sp<sup>2</sup>) and C(sp) Carbon Centers
2014, Comprehensive Organic Synthesis: Second EditionHighly selective palladium-catalyzed Suzuki-Miyaura monocoupling reactions of ethene and arene derivatives bearing two or more electrophilic sites
2011, TetrahedronCitation Excerpt :In fact, it is well known that polychlorinated biphenyls are persistent organic pollutants that are implicated in a number of human diseases, such as reproductive and neurological deficiencies and cancer of the digestive system.109 Table 3 lists the catalyst systems and the reaction conditions used for the synthesis of monochlorinated biphenyls 171a–c (entries 1–4 and 19),98–101,106 171l (entry 13),104 171n–p (entries 15–17),104,105 171r (entry 20)107 and 171s (entry 21),107 and polychlorinated biphenyls 171d–k (entries 5–12),102,103 171m (entry 14)104 and 171q (entry 18)105 from chloroiodoarenes 170 and arylboronic acids or esters. As shown in this table, 4-chlorobiphenyl (171b) was prepared in high yields from 4-chloroiodobenzene (170b) by using three different protocols.
Iron catalyzed hydrodebromination of 2-aryl-1,1-dibromo-1-alkenes
2001, Journal of Organometallic Chemistry