36638-16-1Relevant articles and documents
Synthesis of benzofurans, tetrahydrobenzopyrans, and related cyclic ethers via cyclic carbopalladation
Negishi, Ei-ichi,Nguyen, Thinh,O'Connor, Brian,Evans, Jeffrey M.,Silveira Jr., Augustine
, p. 55 - 58 (1989)
Treatment of a variety of alkenyl ethers (1-8) derived from o-iodophenol, o-iodobenzyl alcohol, and (Z)-3-iodoallyl alcohols with a catalytic amount of Pd(PPh3)4 or Cl2Pd(PPh3)2 in the presence of NEt3 in refluxing CH3CN gives the corresponding cyclic ethers in good yields.
Copper-catalyzed cross-coupling of boronic esters with aryl iodides and application to the carboboration of alkynes and allenes
Zhou, Yiqing,You, Wei,Smith, Kevin B.,Brown, M. Kevin
supporting information, p. 3475 - 3479 (2014/04/03)
Copper-catalyzed Suzuki-Miyaura-type cross-coupling and carboboration processes are reported. The cross-couplings function well with a variety of substituted aryl iodides and aryl boronic esters and allows for orthogonal reactivity compared to palladium-catalyzed processes. The carboboration method includes both alkynes and allenes and provides access to highly substituted and stereodefined vinyl boronic esters. The alkyne carboboration method is highlighted in the simple one-pot synthesis of Tamoxifen. Cross-Cu-pling: The title cross-couplings function well with a variety of substituted aryl iodides and aryl boronic esters and allows for reactivity orthogonal to that of the palladium-catalyzed processes. The title carboboration method includes both alkynes and allenes and provides access to highly substituted and stereodefined vinyl boronic esters. The alkyne carboboration method is highlighted in a simple one-pot synthesis of Tamoxifen.
Synthesis of cyclic ethers from 3- and 4-hydroxyalkylphosphonium salts
Okuma, Kentaro,Sakai, Osami,Hayano, Tetsuji,Shioji, Kosei,Matsuyama, Haruo
, p. 2209 - 2213 (2007/10/03)
The reaction of 6-methylene-1,3-dioxepanes derived from 3-hydroxyalkyltriphenylphosphonium salts and paraformaldehyde with trimethylsilyl trifluoromethanesulfonate in the presence of N,N- diisopropylethylamine yielded novel 4-formyltetrahydropyrans. 3-Met
Cyclodextrin-Promoted Radical Cyclization of o-(2-Propenyloxy)- and o-(2-Propynyloxy)-benzenediazonium Ions
Fukunishi, Koushi,Shimode, Mitsuo,Hisamune, Rie,Akita, Makoto,Kuwabara, Masaki,et al.
, p. 337 - 340 (2007/10/02)
Radical dediazoniation of o-(2-propenyloxy)- and o-(2-propynyloxy)benzenediazonium ions in the presence of β-cyclodextrin gives selectively dihydrobenzofurans under N2, while hydroxymethylated dihydrobenzofurans and 3-hydroxymethyl-benzofuran under air, respectively.
Cobalt-mediated Radical Reactions in Organic Synthesis. Oxidative Cyclisations of Aryl and Alkyl Halides leading to Functionalised Reduced Heterocycles and Butyrolactones
Bhandal, Harcharan,Patel, Vinod F.,Pattenden, Gerald,Russell, Jamie J.
, p. 2691 - 2701 (2007/10/02)
Reactions between the CoI species derived from cobalt(III) salen (11) or cobalt(II) salophen (12) and (O-allyl) or (O-but-3-enyl) iodophenols lead to isolatable cobalt complexes, viz. (16) and (27), which can be converted into substituted benzofurans, i.e. (17) and (23), and benzopyrans, i.e. (28) and (34); similarly, interaction between compound (36) and Co1 salen led in one step to 1,3-dimethylindole (37).Radical cyclisation of the acetal (38a) in the presence of Co1 cobaloxime leads to the cis-ring-fused alkyl cobalt complex (42), which can be converted in a preparative manner into lactone (44) following 1,2-elimination and hydrolysis/oxidation, and into lactone (53) following insertion of molecular oxygen , reduction and hydrolysis/oxidation.
SYNTHESIS OF BENZOFURANS, INDOLES AND BENZOPYRANS VIA OXIDATIVE FREE RADICAL CYCLISATIONS USING COBALT SALEN COMPLEXES.
Patel, Vinod F.,Pattenden, Gerald,Russell, Jamie J.
, p. 2303 - 2306 (2007/10/02)
Reactions between the Co(I) species derived from cobalt(III) 'salen'(1), and (O-allyl) or (O-but-3-enyl)iodophenol, leads to isolatable cobalt complexes, viz (2), (13), which can be converted into substituted benzofurans, i.e. (5), (6) and benzopyrans, i.e. (14), (15); similarly interaction between (18) and Co(I) 'salen' led, in one step, to the 3-methylindole (19).
