2016
DOI: 10.1021/jacs.6b01591
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Asymmetric Alkylation of N-Sulfonylbenzamides with Vinyl Ethers via C–H Bond Activation Catalyzed by Hydroxoiridium/Chiral Diene Complexes

Abstract: Asymmetric alkylation of N-sulfonylbenzamides with vinyl ethers via a directed C-H bond activation gave high yields of the corresponding addition products with high branch- and enantioselectivity.

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Cited by 110 publications
(41 citation statements)
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“…The transition metal‐catalyzed C–H activation of aromatic amides to construct C−C bonds has been extensively used, but there are few reports on the corresponding asymmetric reactions. In 2016, the Yorimitsu team reported the asymmetric alkylation of benzamide with a vinyl ether catalyzed by Ir using amide‐Ms as the directing group (Scheme ) . Using benzamide and vinyl ether as substrates, [Ir(OH)(( S,S )‐Me‐tfb*)] 2 as catalyst and toluene as solvent, the reaction was completed at 70 °C for 20 h. The reaction provides excellent yield and enantioselectivity.…”
Section: Ortho‐c–h Functionalization Of Aromatic Amidesmentioning
confidence: 99%
“…The transition metal‐catalyzed C–H activation of aromatic amides to construct C−C bonds has been extensively used, but there are few reports on the corresponding asymmetric reactions. In 2016, the Yorimitsu team reported the asymmetric alkylation of benzamide with a vinyl ether catalyzed by Ir using amide‐Ms as the directing group (Scheme ) . Using benzamide and vinyl ether as substrates, [Ir(OH)(( S,S )‐Me‐tfb*)] 2 as catalyst and toluene as solvent, the reaction was completed at 70 °C for 20 h. The reaction provides excellent yield and enantioselectivity.…”
Section: Ortho‐c–h Functionalization Of Aromatic Amidesmentioning
confidence: 99%
“…[2] Thea lkylation of C(sp 3 )ÀHb onds with alkenes is obviously one of the useful CÀCb ond formation reactions,a nd in view of the site selectivity of the CÀHb ond activation, the alkylation of the C(sp 3 ) À Hb onds adjacent to an itrogen center [3] has been developed by using transition-metal catalysis [4][5][6][7][8] as well as radical reactions. [11] Ther eaction involves an amidoiridium(I) species as ak ey intermediate derived from the neutral hydroxoiridium and benzamide,a nd the key species undergoes oxidative addition of an ortho-CÀHb ond to form an aryl(hydrido)iridium(III) species.W ea lso reported asymmetric hydroarylation of vinyl ethers using aryl-substituted azoles,containing an N À Hbond as adirecting group,c atalyzed by ah ydroxoiridium/chiral bis(phosphine) complex. [6b,c,e] Recently,wereported that ahydroxoiridium/chiral diene complex catalyzes asymmetric alkylation of N-sulfonylbenzamides with vinyl ethers.…”
mentioning
confidence: 99%
“…Bidentate triarylphosphine ligands,1,2-bis(diphenylphosphino)benzene (dppbz), and rac-binap,w ere less effective than dippbz (entries 2and 3). Thevinyl silane 2k,vinyl ether 2l,and N-vinyl amide 2m and imide 2n also reacted with 1a to give the addition products in good yields (entries [11][12][13][14]. [{Ir-(OH)(cod)} 2 ]i tself displayed al ow catalytic activity in the absence of dippbz, thus giving 3aa in 31 %yield (entry 7).…”
mentioning
confidence: 99%
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“…Since Murai's pioneering work, [5] chiral Rh-catalyzed intramolecular reactions were pioneeringly and comprehensively studied by Bergman and Ellman [6] in termso ft he hydroarylation of variousa lkenes to generate stereogenic centers. For compounds other than indole derivatives, Nishimura [11] recently reported the Ir-catalyzed branch-se-lectiveC ÀHa lkylationo fb enzamide derivatives with various vinyl ethers (Scheme 1b). For compounds other than indole derivatives, Nishimura [11] recently reported the Ir-catalyzed branch-se-lectiveC ÀHa lkylationo fb enzamide derivatives with various vinyl ethers (Scheme 1b).…”
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confidence: 99%