- Synthesis of Functionalized Indolines and Dihydrobenzofurans by Iron and Copper Catalyzed Aryl C-N and C-O Bond Formation
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A simple and effective one-pot, two-step intramolecular aryl C-N and C-O bond forming process for the preparation of a wide range of benzo-fused heterocyclic scaffolds using iron and copper catalysis is described. Activated aryl rings were subjected to a highly regioselective, iron(III) triflimide-catalyzed iodination, followed by a copper(I)-catalyzed intramolecular N-or O-arylation step leading to indolines, dihydrobenzofurans, and six-membered analogues. The general applicability and functional group tolerance of this method were exemplified by the total synthesis of the neolignan natural product, (+)-obtusafuran. DFT calculations using Fukui functions were also performed, providing a molecular orbital rationale for the highly regioselective arene iodination process.
- Henry, Martyn C.,Senn, Hans Martin,Sutherland, Andrew
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p. 346 - 364
(2019/01/08)
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- NAlkylation of tosylamides using esters as primary and tertiary alkyl sources: Mediated by hydrosilanes activated by a ruthenium catalyst
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Select your group: Either a primary or tertiary alkyl group can be selectively introduced onto the nitrogen atom of tosylamides in a ruthenium-catalyzed reaction employing hydrosilanes through a judicious choice in the esters that serve as the alkyl source (see scheme; Ts= 4-toluenesulfonyl). These N-alkylation reactions are useful for construction of naturally occurring azacyclic skeletons. Copyright
- Nishikata, Takashi,Nagashima, Hideo
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supporting information; experimental part
p. 5363 - 5366
(2012/07/03)
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- Regioselective rhodium(I)-catalyzed hydroarylation of protected allylic amines with arylboronic acids
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A novel regioselective rhodium(I)-catalyzed hydroarylation of unactivated alkenes with arylboronic acids is described. The catalytic system employs [Rh(COD)OH]2 and BINAP to effect the addition of various arylboronic acids to protected allylic amines. The regioselectivity was found to be highly dependent on the protecting group, favoring the linear addition product with up to 92% yield and >20:1 regioselectivity.
- Tsui, Gavin Chit,Menard, Frederic,Lautens, Mark
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supporting information; experimental part
p. 2456 - 2459
(2010/07/06)
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