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Literature DB >> 24077102

Divergent Reaction Pathways for Phenol Arylation by Arynes: Synthesis of Helicenes and 2-Arylphenols.

Abstract

Two reactions of phenols with arynes have been developed. If LiTMP base is employed, arynes generated from aryl chlorides react with phenols to form helicenes. o-Arylation of phenols can be achieved by employing tBuONa base in the presence of AgOAc. Direct arylation of binol was achieved leading to the shortest pathway to o,o'-diarylbinols.

Entities: Chemical Disease

Year: 2013 PMID： 24077102 PMCID： PMC3783345 DOI： 10.1039/c2sc21288a

Source DB: PubMed Journal: Chem Sci ISSN： 2041-6520 Impact factor: 9.825

22 in total

1. A highly para-selective copper(II)-catalyzed direct arylation of aniline and phenol derivatives.

Authors: Claire-Lise Ciana; Robert J Phipps; Jochen R Brandt; Falco-Magnus Meyer; Matthew J Gaunt
Journal: Angew Chem Int Ed Engl Date: 2011-01-10 Impact factor: 15.336

2. Palladium-catalyzed ortho-arylation of O-phenylcarbamates with simple arenes and sodium persulfate.

Authors: Xiaodan Zhao; Charles S Yeung; Vy M Dong
Journal: J Am Chem Soc Date: 2010-04-28 Impact factor: 15.419

3. The catalytic intermolecular orthoarylation of phenols.

Authors: Robin B Bedford; Simon J Coles; Michael B Hursthouse; Michael E Limmert
Journal: Angew Chem Int Ed Engl Date: 2003-01-03 Impact factor: 15.336

4. Efficient anodic and direct phenol-arene C,C cross-coupling: the benign role of water or methanol.

Authors: Axel Kirste; Bernd Elsler; Gregor Schnakenburg; Siegfried R Waldvogel
Journal: J Am Chem Soc Date: 2012-02-13 Impact factor: 15.419

5. Indolyne experimental and computational studies: synthetic applications and origins of selectivities of nucleophilic additions.

Authors: G-Yoon J Im; Sarah M Bronner; Adam E Goetz; Robert S Paton; Paul H-Y Cheong; K N Houk; Neil K Garg
Journal: J Am Chem Soc Date: 2010-11-29 Impact factor: 15.419

6. Carbocyclization of aromatic iodides, bicyclic alkenes, and benzynes involving a palladium-catalyzed C-H bond activation as a key step.

Authors: Sivakolundu Bhuvaneswari; Masilamani Jeganmohan; Chien-Hong Cheng
Journal: Org Lett Date: 2006-11-23 Impact factor: 6.005

7. Transition-metal-free alkynylation of aryl chlorides.

Authors: Thanh Truong; Olafs Daugulis
Journal: Org Lett Date: 2011-07-25 Impact factor: 6.005

8. Palladium-catalysed ortho-arylation of carbamate-protected phenols.

Authors: Robin B Bedford; Ruth L Webster; Charlotte J Mitchell
Journal: Org Biomol Chem Date: 2009-09-30 Impact factor: 3.876

9. TBDPS and Br-TBDPS protecting groups as efficient aryl group donors in Pd-catalyzed arylation of phenols and anilines.

Authors: Chunhui Huang; Vladimir Gevorgyan
Journal: J Am Chem Soc Date: 2009-08-12 Impact factor: 15.419

10. Mechanisms of osteoclastogenesis inhibition by a novel class of biphenyl-type cannabinoid CB(2) receptor inverse agonists.

Authors: Wolfgang Schuehly; Juan Manuel Viveros Paredes; Jonas Kleyer; Antje Huefner; Sharon Anavi-Goffer; Stefan Raduner; Karl-Heinz Altmann; Jürg Gertsch
Journal: Chem Biol Date: 2011-08-26

13 in total

1. Sydnone-Based Approach to Heterohelicenes through 1,3-Dipolar-Cycloadditions.

Authors: Expédite Yen-Pon; Pier Alexandre Champagne; Lucie Plougastel; Sandra Gabillet; Pierre Thuéry; Mizuki Johnson; Gilles Muller; Grégory Pieters; Frédéric Taran; K N Houk; Davide Audisio
Journal: J Am Chem Soc Date: 2019-01-15 Impact factor: 15.419

2. 1,2-Bis(arylthio)arene synthesis via aryne intermediates.

Authors: Milad Mesgar; Justin Nguyen-Le; Olafs Daugulis
Journal: Chem Commun (Camb) Date: 2019-08-07 Impact factor: 6.222

3. Silylaryl Halides Can Replace Triflates as Aryne Precursors.

Authors: Milad Mesgar; Olafs Daugulis
Journal: Org Lett Date: 2016-07-14 Impact factor: 6.005

4. Synthesis of 1,2-Bis(trifluoromethylthio)arenes via Aryne Intermediates.

Authors: Milad Mesgar; Olafs Daugulis
Journal: Org Lett Date: 2017-07-28 Impact factor: 6.005

5. Reactions of hexadehydro-Diels-Alder benzynes with structurally complex multifunctional natural products.

Authors: Sean P Ross; Thomas R Hoye
Journal: Nat Chem Date: 2017-02-27 Impact factor: 24.427

6. Aryne cycloaddition reactions of benzodioxasilines as aryne precursors generated by catalytic reductive ortho-C-H silylation of phenols with traceless acetal directing groups.

Authors: Parham Asgari; Udaya Sree Dakarapu; Hiep H Nguyen; Junha Jeon
Journal: Tetrahedron Date: 2016-12-08 Impact factor: 2.457