Publication

Palladium-Catalyzed Divergent Cyclopropanation by Regioselective Solvent-Driven C(sp(3))-H Bond Activation

조회수 : 292 등록일 : 2019.01.07 00:00

저자 : Lee, JS (Lee, Jae Sung); Lee, WK (Lee, Won Koo)
출처 : ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
출판일 : 2018.11.19


Palladium-Catalyzed Divergent Cyclopropanation by Regioselective Solvent-Driven C(sp(3))-H Bond Activation


Chung, DS (Chung, Da Sol)1 ] ; Lee, JS (Lee, Jae Sung)2 ] Ryu, H (Ryu, Ho)3,4 ] Park, J (Park, Jiyong)3,4 ] Kim, H (Kim, Hyunjoong)3,4 ] Lee, JH(Lee, Joo Hyun)1 ] Kim, UB (Kim, U. Bin)1 ] Lee, WK (Lee, Won Koo)2 ] Baik, MH (Baik, Mu-Hyun)3,4 ] Lee, SG (Lee, Sang-gi)1 ]


[ 1 ] Ewha Womans Univ, Dept Chem & Nanosci BK21 PLUS, Seoul 03760, South Korea
[ 2 ] Sogang Univ, Dept Chem, Seoul 04107, South Korea
[ 3 ] Korea Adv Inst Sci & Technol, Dept Chem, Daejeon 34141, South Korea
[ 4 ] Inst for Basic Sci Korea, Ctr Catalyt Hydrocarbon Functionalizat, Daejeon 34141, South Korea



Reported is a tandem palladium-catalyzed Heck/regioselective C(sp(3))-H activation reaction for the divergent synthesis of spiro- and fused-cyclopropanated indolines from N-methallylated 2-bromoarylamides. The regioselectivity of the C-H bond activation in the s-alkylPdII intermediate is controlled by the solvent used. DFT calculations suggest that the polarity of solvent molecules could influence the transition-state energy, leading to a bifurcation of the C-H bond activation in the s-alkylPdII intermediate.






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