Base-catalyzed efficient tandem [3 + 3] and [3 + 2 + 1] annulation-aerobic oxidative benzannulations.

An efficient synthesis of substituted benzenes via a base-catalyzed [3 + 3] aerobic oxidative aromatization of α,β-unsaturated carbonyl compounds with dimethyl glutaconate was reported. All the reactions were carried out under mild, metal-free conditions to afford the products in high to excellent yields with molecular oxygen as the sole oxidant and water as the sole byproduct. Furthermore, a more convenient tandem [3 + 2 + 1] aerobic oxidative aromatization reaction was developed through the in situ generation of the α,β-unsaturated carbonyl compounds from aldehydes and ketones.

[1]  D. Tejedor,et al.  Chemo-differentiating ABB' multicomponent reactions. Privileged building blocks. , 2007, Chemical Society reviews.

[2]  U. Siemeling,et al.  One-step synthesis of polysubstituted benzene derivatives by multi-component cyclization of alpha-bromoacetate, malononitrile and aromatic aldehydes. , 2008, Chemical communications.

[3]  A. Mazzanti,et al.  Organocatalytic asymmetric formal [3 + 2] cycloaddition with in situ-generated N-carbamoyl nitrones. , 2009, Journal of the American Chemical Society.

[4]  D. Dong,et al.  A facile and efficient one-pot synthesis of polysubstituted benzenes in guanidinium ionic liquids , 2010 .

[5]  Qun Liu,et al.  Synthesis of acridines and persubstituted phenols from cyclobutenones and active methylene ketones. , 2012, The Journal of organic chemistry.

[6]  G. Schnakenburg,et al.  Heterobimetallic dibenzoindenyl (Cr(CO)3-Re(CO)3) complexes via chromium-templated [3 + 2 + 1]benzannulation: synthesis and molecular structures. , 2011, Inorganic chemistry.

[7]  V. Snieckus.  Directed aromatic functionalization , 2011, Beilstein journal of organic chemistry.

[8]  Bing Li,et al.  [5 + 1] annulation: a synthetic strategy for highly substituted phenols and cyclohexenones. , 2005, Journal of the American Chemical Society.

[9]  Hao Li,et al.  Direct transformation of simple enals to 3,4-disubstituted benzaldehydes under mild reaction conditions via an organocatalytic regio- and chemoselective dimerization cascade. , 2012, Chemistry.

[10]  Dawei Zhang,et al.  Double isocyanide cyclization: a synthetic strategy for two-carbon-tethered pyrrole/oxazole pairs. , 2011, Journal of the American Chemical Society.

[11]  A. Padwa,et al.  A benzannulation protocol to prepare substituted aryl amines using a Michael-aldol reaction of beta-keto sulfones. , 2009, The Journal of organic chemistry.

[12]  Penchal Reddy Nandaluru,et al.  Multicomponent synthesis of 6H-dibenzo[b,d]pyran-6-ones and a total synthesis of cannabinol. , 2012, Organic letters.

[13]  S. Stahl,et al.  Palladium-Catalyzed Aerobic Dehydrogenation of Substituted Cyclohexanones to Phenols , 2011, Science.

[14]  Peter Langer,et al.  [3+3] cyclizations of 1,3-bis(silyl enol ether)s with 1,1-diacetylcyclopentane and 1,1-diacetylcyclopropane. , 2003, Angewandte Chemie.

[15]  Jianli Li,et al.  Cu(OAc)2/TFA-promoted formal [3 + 3] cycloaddition/oxidation of enamines and enones for synthesis of multisubstituted aromatic amines. , 2012, Organic letters.

[16]  P. Langer.  Synthesis of Fluorinated Arenesand Hetarenes Based on One-Pot Cyclizations of 1,3-Bis(trimethylsilyloxy)-1,3-butadienes , 2009 .

[17]  M. G. Hutchings,et al.  A remarkably simple and efficient benzannulation reaction. , 2007, Angewandte Chemie.

[18]  Y. Huang,et al.  Phosphine-mediated domino benzannulation strategy for the construction of highly functionalized multiaryl skeletons. , 2012, Chemistry.

[19]  Alessandro Palmieri,et al.  Nitroalkanes as new, ideal precursors for the synthesis of benzene derivatives. , 2008, Chemical communications.

[20]  P. Wessig,et al.  The dehydro-Diels-Alder reaction. , 2008, Chemical reviews.

[21]  S. Kirsch,et al.  Electrophilic cyclization of 1,5-enynes. , 2010, Angewandte Chemie.

[22]  Qun Liu,et al.  Direct synthesis of highly substituted 2-cyclohexenones and sterically hindered benzophenones based on a [5C + 1C] annulation. , 2009, The Journal of organic chemistry.

[23]  J. Wang,et al.  Rh(I)-catalyzed carbonylative carbocyclization of tethered ene- and yne-cyclopropenes. , 2010, Organic letters.

[24]  Junliang Zhang,et al.  Rhodium-catalyzed tandem heterocyclization and carbonylative [(3+2)+1] cyclization of diyne-enones. , 2011, Organic letters.

[25]  Jae Nyoung Kim,et al.  Synthesis of poly-substituted nitrobenzene derivatives from Baylis-Hillman adducts via [3+3] annulation protocol , 2007 .

[26]  Karl Heinz Dötz,et al.  Fischer carbene complexes in organic synthesis: metal-assisted and metal-templated reactions. , 2009, Chemical reviews.

[27]  Bruce Ganem,et al.  Strategies for innovation in multicomponent reaction design. , 2009, Accounts of chemical research.

[28]  R. Orru,et al.  1-Azadienes in cycloaddition and multicomponent reactions towards N-heterocycles. , 2008, Chemical communications.

[29]  Alan R. Katritzky,et al.  [3+3] Benzannulations of benzenoid- and heteroaromatic-ring systems , 1999 .

[30]  Jun Liu,et al.  Tandem [4 + 1 + 1] annulation and metal-free aerobic oxidative aromatization: straightforward synthesis of highly substituted phenols from one aldehyde and two ketones. , 2010, Chemical communications.

[31]  Nilanjana Majumdar,et al.  Simultaneous synthesis of both rings of chromenes via a benzannulation/o-quinone methide formation/electrocyclization cascade. , 2012, Journal of the American Chemical Society.

[32]  D. Astruc.  Modern Arene Chemistry , 2002 .

[33]  Elisabetta Brenna,et al.  Recent advances in the benzannulation of substituted 3-alkoxycarbonyl-3,5-hexadienoic acids and 3-alkoxycarbonylhex-3-en-5-ynoic acids to polysubstituted aromatics. , 2007, Chemistry.

[34]  Dennis G Hall,et al.  Natural product synthesis using multicomponent reaction strategies. , 2009, Chemical reviews.