Literature DB >> 22758657

Iron-catalyzed alkylations of aryl sulfamates and carbamates.

Amanda L Silberstein1, Stephen D Ramgren, Neil K Garg.   

Abstract

The alkylation of aryl sulfamates and carbamates using iron catalysis is reported. The method constructs sp(2)-sp(3) carbon-carbon bonds and provides synthetically useful yields across a range of substrates (>35 examples). The directing group ability of sulfamates and carbamates, accompanied by their low reactivity toward conventional cross-couplings, renders these substrates useful for the synthesis of polyfunctionalized arenes.

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Year:  2012        PMID: 22758657      PMCID: PMC3479317          DOI: 10.1021/ol301681z

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  35 in total

1.  Transition-metal-free Suzuki-type coupling reactions.

Authors:  Nicholas E Leadbeater; Maria Marco
Journal:  Angew Chem Int Ed Engl       Date:  2003-03-28       Impact factor: 15.336

2.  Directed ortho borylation of phenol derivatives catalyzed by a silica-supported iridium complex.

Authors:  Kenji Yamazaki; Soichiro Kawamorita; Hirohisa Ohmiya; Masaya Sawamura
Journal:  Org Lett       Date:  2010-09-17       Impact factor: 6.005

3.  A reassessment of the transition-metal free suzuki-type coupling methodology.

Authors:  Riina K Arvela; Nicholas E Leadbeater; Michael S Sangi; Victoria A Williams; Patricia Granados; Robert D Singer
Journal:  J Org Chem       Date:  2005-01-07       Impact factor: 4.354

4.  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

5.  Heteroaromatic sulfonates and phosphates as electrophiles in iron-catalyzed cross-couplings.

Authors:  Thomas M Gøgsig; Anders T Lindhardt; Troels Skrydstrup
Journal:  Org Lett       Date:  2009-11-05       Impact factor: 6.005

6.  Rhodium-catalyzed selective C-H activation/olefination of phenol carbamates.

Authors:  Tian-Jun Gong; Bin Xiao; Zhao-Jing Liu; Jian Wan; Jun Xu; Dong-Fen Luo; Yao Fu; Lei Liu
Journal:  Org Lett       Date:  2011-05-23       Impact factor: 6.005

7.  Rhodium-catalyzed direct ortho C-H olefination of phenol derivatives.

Authors:  Chao Feng; Teck-Peng Loh
Journal:  Chem Commun (Camb)       Date:  2011-08-18       Impact factor: 6.222

8.  Suzuki-Miyaura cross-coupling of aryl carbamates and sulfamates: experimental and computational studies.

Authors:  Kyle W Quasdorf; Aurora Antoft-Finch; Peng Liu; Amanda L Silberstein; Anna Komaromi; Tom Blackburn; Stephen D Ramgren; K N Houk; Victor Snieckus; Neil K Garg
Journal:  J Am Chem Soc       Date:  2011-04-01       Impact factor: 15.419

9.  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

10.  N,N-diethyl O-carbamate: directed metalation group and orthogonal Suzuki-Miyaura cross-coupling partner.

Authors:  Aurora Antoft-Finch; Tom Blackburn; Victor Snieckus
Journal:  J Am Chem Soc       Date:  2009-12-16       Impact factor: 15.419

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  8 in total

1.  Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis.

Authors:  Timothy B Boit; Ana S Bulger; Jacob E Dander; Neil K Garg
Journal:  ACS Catal       Date:  2020-09-10       Impact factor: 13.084

2.  Combined Effects of Backbone and N-Substituents on Structure, Bonding, and Reactivity of Alkylated Iron(II)-NHCs.

Authors:  Salvador B Muñoz; Valerie E Fleischauer; William W Brennessel; Michael L Neidig
Journal:  Organometallics       Date:  2018-09-06       Impact factor: 3.876

3.  Photochemically-Mediated, Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamate Esters.

Authors:  J Miles Blackburn; Anastasia L Gant Kanegusuku; Georgia E Scott; Jennifer L Roizen
Journal:  Org Lett       Date:  2019-08-22       Impact factor: 6.005

4.  Enantioselective alkylative cross-coupling of unactivated aromatic C-O electrophiles.

Authors:  Zishuo Zhang; Jintong Zhang; Quan Gao; Yu Zhou; Mingyu Yang; Haiqun Cao; Tingting Sun; Gen Luo; Zhi-Chao Cao
Journal:  Nat Commun       Date:  2022-05-26       Impact factor: 17.694

5.  Bright Side of Lignin Depolymerization: Toward New Platform Chemicals.

Authors:  Zhuohua Sun; Bálint Fridrich; Alessandra de Santi; Saravanakumar Elangovan; Katalin Barta
Journal:  Chem Rev       Date:  2018-01-16       Impact factor: 60.622

6.  Pd-catalyzed Suzuki-Miyaura cross-coupling reactions between sulfamates and potassium Boc-protected aminomethyltrifluoroborates.

Authors:  Gary A Molander; Inji Shin
Journal:  Org Lett       Date:  2013-05-06       Impact factor: 6.005

7.  NHC and nucleophile chelation effects on reactive iron(ii) species in alkyl-alkyl cross-coupling.

Authors:  Valerie E Fleischauer; Salvador B Muñoz Iii; Peter G N Neate; William W Brennessel; Michael L Neidig
Journal:  Chem Sci       Date:  2018-01-08       Impact factor: 9.825

8.  Iron-catalysed allylation-hydrogenation sequences as masked alkyl-alkyl cross-couplings.

Authors:  Josef Bernauer; Guojiao Wu; Axel Jacobi von Wangelin
Journal:  RSC Adv       Date:  2019-10-02       Impact factor: 4.036

  8 in total

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