title: Cyclization strategies to polyenes using Pd(II)-catalyzed couplings of pinacol vinylboronates.
abstract: As a complement to Pd(0)-catalyzed cyclizations, seven Pd(II)-catalyzed cyclization strategies are reported. α,ω-Diynes are selectively hydroborated to bis(boronate esters), which cyclize under Pd(II)-catalysis producing a diverse array of small, medium, and macrocyclic polyenes with controlled E,E, Z,Z, or E,Z stereochemistry. Various functional groups are tolerated including aryl bromides, and applications are illustrated.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.
authors.forename: Robert G
authors.initials: RG
authors.lastname: Iafe
authors.forename: Daniel G
authors.initials: DG
authors.lastname: Chan
authors.forename: Jonathan L
authors.initials: JL
authors.lastname: Kuo
authors.forename: Byron A
authors.initials: BA
authors.lastname: Boon
authors.forename: Darius J
authors.initials: DJ
authors.lastname: Faizi
authors.forename: Tomomi
authors.initials: T
authors.lastname: Saga
authors.forename: Jonathan W
authors.initials: JW
authors.lastname: Turner
authors.forename: Craig A
authors.initials: CA
authors.lastname: Merlic
mesh_terms: D002384:Catalysis; D003500:Cyclization; D053280:Diynes / Q000737:chemistry*; D004952:Esters; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011090:Polyenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry
chemical_list: D053280:Diynes; D004952:Esters; D011090:Polyenes; D014753:Vinyl Compounds; C519434:vinylboronate ester; D010165:Palladium