BOND FORMATION;
INNER-SPHERE;
FLUORINE;
CYCLOPROPANES;
ELIMINATION;
PHOSPHATES;
MECHANISM;
D O I:
10.1039/d4qo01800a
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
The palladium-catalyzed cross-coupling of (E)-2-fluoroallyl carbonates and allylboronates is reported. The regioselectivity is susceptive to the steric requirements of the NHC ligand, with small IMes favoring linear fluorinated 1,5-dienes, while IPrBIDEA featuring sterically-congested character benefits branched products. Control experiments revealed that either 2-fluoroallyl carbonates or gem-F2CPs could undergo allylation with excellent regioselectivity, yet the former showed somewhat lower branched reactivity.
机构:
Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USAUniv Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
Handa, Sachin
Andersson, Martin P.
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机构:
Univ Copenhagen, Nanosci Ctr, Dept Chem, DK-1168 Copenhagen, DenmarkUniv Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
Andersson, Martin P.
Gallou, Fabrice
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机构:
Novartis Pharma AG, Basel, SwitzerlandUniv Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
Gallou, Fabrice
Reilly, John
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机构:
Novartis Inst Med Res, Cambridge, MA 02139 USAUniv Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
Reilly, John
Lipshutz, Bruce H.
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机构:
Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USAUniv Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
机构:
Tokyo Univ Agr & Technol, Dept Appl Chem, Grad Sch Engn, Koganei, Tokyo 1848588, JapanTokyo Univ Agr & Technol, Dept Appl Chem, Grad Sch Engn, Koganei, Tokyo 1848588, Japan
Mitsui, Tatsuo
Kikuchi, Shu
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h-index: 0
机构:
Tokyo Univ Agr & Technol, Dept Appl Chem, Grad Sch Engn, Koganei, Tokyo 1848588, JapanTokyo Univ Agr & Technol, Dept Appl Chem, Grad Sch Engn, Koganei, Tokyo 1848588, Japan