caa a22 4500 605512221 CHVBK 20210128100654.0 cr unu---uuuuu 210128e20151001xx s 000 0 eng 10.1007/s00894-015-2802-2 doi (NATIONALLICENCE)springer-10.1007/s00894-015-2802-2 DFT studies on the palladium-catalyzed dearomatization reaction between naphthalene allyl chloride and allyltributylstannane [Elektronische Daten] [Wei Cao, Dongxu Tian, Dongxue Han] The Pd-catalyzed dearomatization of naphthalene allyl chloride with allyltributylstannane has been investigated using density functional theory (DFT) calculations at the B3LYP level. The calculations indicate that the (ŋ 1 -allyl)(ŋ 3 -allyl)Pd(PH3) complex is responsible for the formation of ortho-dearomatized product. Moreover it is easy to produce the ortho-dearomatized product when reductive elimination starts from (ŋ 3 -allylnaphthalene)(ŋ 1 -allyl)Pd complex 7, while it is easy to form the para-dearomatized product when reductive elimination starts from (ŋ 3 -allylnaphthalene)(ŋ 1 -allyl)Pd complex 9. The Stille coupling products can't be produced due to high reaction energy barrier. Graphical Abstract Two mechanisms of dearomatization are investigated by DFT, and (ŋ 1 -allyl)(ŋ 3 -allyl)Pd(PH3) complexes are the main intermediates for ortho-dearomatized product. Springer-Verlag Berlin Heidelberg, 2015 Dearomatization nationallicence DFT nationallicence NBO nationallicence Propenylnaphthalene nationallicence Cao Wei State Key Laboratory of Fine Chemicals, Dalian University of Technology, 116024, Dalian, China aut Tian Dongxu State Key Laboratory of Fine Chemicals, Dalian University of Technology, 116024, Dalian, China aut Han Dongxue State Key Laboratory of Fine Chemicals, Dalian University of Technology, 116024, Dalian, China aut Journal of Molecular Modeling Springer Berlin Heidelberg 21/10(2015-10-01), 1-7 1610-2940 21:10<1 2015 21 894 https://doi.org/10.1007/s00894-015-2802-2 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1007/s00894-015-2802-2 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Cao Wei State Key Laboratory of Fine Chemicals, Dalian University of Technology, 116024, Dalian, China aut NATIONALLICENCE 700 1- Tian Dongxu State Key Laboratory of Fine Chemicals, Dalian University of Technology, 116024, Dalian, China aut NATIONALLICENCE 700 1- Han Dongxue State Key Laboratory of Fine Chemicals, Dalian University of Technology, 116024, Dalian, China aut NATIONALLICENCE 773 0- Journal of Molecular Modeling Springer Berlin Heidelberg 21/10(2015-10-01), 1-7 1610-2940 21:10<1 2015 21 894