Intramolecular Palladium-Catalyzed Ring Opening of Oxabenzonorbornadienes with C1-Tethered Aryl Halides.

The novel intramolecular ring opening of oxabenzonorbornadienes with C1-tethered aryl halides was investigated using palladium catalysts to form fused tetracyclic frameworks. The reaction was generally found to synthesize 1,2-dihydronaphthalen-1-ol products with mild selectivity but was capable of synthesizing dehydrated naphthalene products in excellent yield and selectivity. Substituent effects on oxabenzonorbornadiene and on the iodoarene were explored along with the effects of varying tether length, where an efficient reaction was observed in nearly all cases. A total of 16 examples are reported with yields ranging from 0 to 96%.

[1]  Wen Yang,et al.  Water‐Promoted Palladium‐Catalyzed Asymmetric Ring‐Opening of Oxabenzonorbornadienes with Alkoxysilanes , 2020 .

[2]  W. Tam,et al.  Acid-catalyzed intramolecular ring-opening reactions of cyclopropanated oxabenzonorbornadienes with alcohol nucleophiles , 2019, Tetrahedron Letters.

[3]  Huanyong Li,et al.  Palladium-catalyzed syn-stereocontrolled ring-opening of oxabicyclic alkenes with arylsulfonyl hydrazides. , 2019, The Journal of organic chemistry.

[4]  W. Tam,et al.  Palladium/Lewis Acid Cocatalyzed Ring-Opening Reactions of Unsymmetrical Oxabenzonobornadienes with Oximes. , 2019, The Journal of organic chemistry.

[5]  W. Tam,et al.  Recent Advances in Transition Metal-Catalyzed Reactions of Oxabenzonorborn-adiene , 2019, Current organic synthesis.

[6]  Q. Kang,et al.  Rhodium-Catalyzed Allylation Reactions , 2019, Synthesis.

[7]  Hao Zhang,et al.  Asymmetric Hydrophosphination of Heterobicyclic Alkenes: Facile Access to Phosphine Ligands for Asymmetric Catalysis , 2019, ACS Catalysis.

[8]  Wei Zhang,et al.  Asymmetric Ring-Opening Reactions of Aza- and Oxa-bicyclic Alkenes with Boronic Acids Using a Palladium/Zinc Co-catalytic System. , 2017, The Journal of organic chemistry.

[9]  W. Tam,et al.  Palladium-catalyzed ring-opening reactions of cyclopropanated 7-oxabenzonorbornadiene with alcohols , 2016, Beilstein journal of organic chemistry.

[10]  M. Lautens,et al.  Rhodium-Catalyzed Asymmetric Cycloisomerization and Parallel Kinetic Resolution of Racemic Oxabicycles. , 2016, Angewandte Chemie.

[11]  Wen Yang,et al.  Palladium-Catalyzed syn-Stereocontrolled Ring-Opening of Oxabicyclic Alkenes with Sodium Arylsulfinates. , 2016, The Journal of organic chemistry.

[12]  T. Hiyama,et al.  Dehydrogenative Carbon-Carbon Bond Formation Using Alkynyloxy Moieties as Hydrogen-Accepting Directing Groups. , 2015, Angewandte Chemie.

[13]  Hui Zhou,et al.  Triarylphosphines as Aryl Donors for Pd(II)-Catalyzed Aromatic Coupling of Oxabenzonorbornadienes. , 2015, Organic letters.

[14]  Cheng-Yuan Lin,et al.  Palladium/Silver-Cocatalyzed Tandem Reactions of Oxabenzonorbornadienes with Substituted Arylacetylenes: A Simple Method for the Preparation of 1,2-Diarylethanones and 1,2-Diarylacetylenes , 2015 .

[15]  Jun Wang,et al.  Palladium/Zinc Co-Catalyzed syn-Stereoselectively Asymmetric Ring-Opening Reaction of Oxabenzonorbornadienes with Phenols. , 2015, Chemistry.

[16]  TamWilliam,et al.  Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabenzonorbornadienes , 2014 .

[17]  Mikhail O. Konev,et al.  Enantiospecific Intramolecular Heck Reactions of Secondary Benzylic Ethers , 2014, Journal of the American Chemical Society.

[18]  M. Lautens,et al.  Diastereoselective Friedel-Crafts alkylation of hydronaphthalenes. , 2011, The Journal of organic chemistry.

[19]  P. Guiry,et al.  The asymmetric Heck and related reactions. , 2011, Chemical Society reviews.

[20]  K. Endo,et al.  Multinuclear Pd/Zn complex-catalyzed asymmetric alkylative ring-opening reaction of oxabicyclic alkenes. , 2011, Organic letters.

[21]  W. Tam,et al.  Thieme Chemistry Journal Awardees — Where Are They Now? Bicyclic Alkenes: From Cycloadditions to the Discovery of New Reactions , 2010 .

[22]  Junliang Zhang,et al.  Tetrasubstituted furans by Pd(II)-catalyzed three-component domino reactions of 2-(1-alkynyl)-2-alken-1-ones with nucleophiles and vinyl ketones or acrolein. , 2009, Chemistry.

[23]  M. Lautens,et al.  Reagent-controlled regiodivergent resolution of unsymmetrical oxabicyclic alkenes using a cationic rhodium catalyst. , 2009, Journal of the American Chemical Society.

[24]  Chien‐Hong Cheng,et al.  New catalytic reactions of oxa- and azabicyclic alkenes. , 2007, Accounts of chemical research.

[25]  S. Martin,et al.  Pd-catalyzed ring opening of oxa- and azabicyclic alkenes with aryl and vinyl halides: efficient entry to 2-substituted 1,2-dihydro-1-naphthols and 2-substituted 1-naphthols. , 2006, The Journal of organic chemistry.

[26]  L. Overman,et al.  Diastereoselection in the formation of spirocyclic oxindoles by the intramolecular Heck reaction. , 2006, The Journal of organic chemistry.

[27]  L. Overman,et al.  Use of the intramolecular Heck reaction for forming congested quaternary carbon stereocenters. Stereocontrolled total synthesis of (+/-)-gelsemine. , 2005, Journal of the American Chemical Society.

[28]  M. Oestreich.  Neighbouring‐Group Effects in Heck Reactions , 2005 .

[29]  S. Martin,et al.  Facile synthesis of 2-substituted 1,2-dihydro-1-naphthols and 2-substituted 1-naphthols. , 2004, Organic letters.

[30]  R. Guy,et al.  Synthesis of medium ring heterocycles using an intramolecular Heck reaction. , 2004, Organic letters.

[31]  M. Lautens,et al.  Scope of palladium-catalyzed alkylative ring opening. , 2004, Journal of the American Chemical Society.

[32]  M. Lautens,et al.  Palladium(II) catalyst systems for the addition of boronic acids to bicyclic alkenes: new scope and reactivity. , 2003, Organic letters.

[33]  M. Lautens,et al.  Synthesis of novel tetracycles via an intramolecular Heck reaction with anti-hydride elimination. , 2003, Organic letters.

[34]  L. Overman,et al.  The asymmetric intramolecular Heck reaction in natural product total synthesis. , 2003, Chemical reviews.

[35]  Chien‐Hong Cheng,et al.  Asymmetric reductive ring-opening of bicyclic olefins catalyzed by palladium and nickel complexes. , 2003, Organic letters.

[36]  Yoshinori Yamamoto,et al.  Pd(II) acts simultaneously as a Lewis acid and as a transition-metal catalyst: synthesis of cyclic alkenyl ethers from acetylenic aldehydes. , 2002, Journal of the American Chemical Society.

[37]  I. Beletskaya,et al.  The heck reaction as a sharpening stone of palladium catalysis. , 2000, Chemical reviews.

[38]  Chien‐Hong Cheng,et al.  Nickel-Catalyzed Highly Stereoselective Ring Opening of 7-Oxa- and Azanorbornenes with Organic Halides. , 1999, The Journal of organic chemistry.

[39]  Chien‐Hong Cheng,et al.  Palladium-Catalyzed Reductive Couplings of Organic Halides with 7-Heteroatom Norbornadienes. New Synthetic Methods for Substituted Aryls and cis-1,2-Dihydro-1-naphthyl Alcohols and Carbamates , 1995 .

[40]  M. Lautens,et al.  A New Strategy to Bicyclo[5.3.0]decenes via Anionic Intramolecular Ring Opening of Oxabicyclo[3.2.1] Compounds , 1995 .

[41]  A. Meijere,et al.  Fine Feathers Make Fine Birds: The Heck Reaction in Modern Garb† , 1995 .

[42]  H. Hart,et al.  Scope of tandem cycloadditon/radical cyclization methodology , 1989 .

[43]  H. Hart,et al.  Tandem cycloaddition/radical cyclization, a widely applicable strategy for the rapid assembly of polycyclic systems , 1988 .

[44]  M. Lautens,et al.  Transition metal-catalyzed enantioselective ring-opening reactions of oxabicyclic alkenes. , 2003, Accounts of chemical research.

[45]  G. Crisp.  Variations on a theme—recent developments on the mechanism of the Heck reaction and their implications for synthesis , 1998 .