Literature DB >> 19929001

Palladium-catalyzed hydroalkylation of styrenes with organozinc reagents to form carbon-carbon sp3-sp3 bonds under oxidative conditions.

Kaveri Balan Urkalan1, Matthew S Sigman.   

Abstract

An unconventional route for the formation of sp(3)-sp(3) C-C bonds from various styrenes and an organozinc reagent in a formal alkene hydroalkylation process is detailed. Mechanistically, this process is proposed to proceed by initial transmetalation followed by formation of a Pd-H species, which is subsequently trapped by the styrene.

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Year:  2009        PMID： 19929001      PMCID： PMC2794962          DOI： 10.1021/ja908545b

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  15 in total

1.  Suzuki cross-couplings of alkyl tosylates that possess beta hydrogen atoms: synthetic and mechanistic studies.

Authors:  Matthew R Netherton; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2002-10-18       Impact factor: 15.336

2.  Advances in functional-group-tolerant metal-catalyzed alkyl-alkyl cross-coupling reactions.

Authors:  Diego J Cárdenas
Journal:  Angew Chem Int Ed Engl       Date:  2003-01-27       Impact factor: 15.336

3.  Oxidative cross-coupling through double transmetallation: surprisingly high selectivity for palladium-catalyzed cross-coupling of alkylzinc and alkynylstannanes.

Authors:  Yingsheng Zhao; Haibo Wang; Xiaohui Hou; Yanhe Hu; Aiwen Lei; Heng Zhang; Lizheng Zhu
Journal:  J Am Chem Soc       Date:  2006-11-29       Impact factor: 15.419

4.  Catalysts for cross-coupling reactions with non-activated alkyl halides.

Authors:  Anja C Frisch; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2005-01-21       Impact factor: 15.336

5.  Catalytic enantioselective Negishi reactions of racemic secondary benzylic halides.

Authors:  Forrest O Arp; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2005-08-03       Impact factor: 15.419

6.  Efficient synthesis of functionalized organozinc compounds by the direct insertion of zinc into organic iodides and bromides.

Authors:  Arkady Krasovskiy; Vladimir Malakhov; Andrei Gavryushin; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2006-09-11       Impact factor: 15.336

7.  Palladium-catalyzed reductive coupling of styrenes and organostannanes under aerobic conditions.

Authors:  Keith M Gligorich; Sarah A Cummings; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2007-10-27       Impact factor: 15.419

Review 8.  Secondary alkyl halides in transition-metal-catalyzed cross-coupling reactions.

Authors:  Alena Rudolph; Mark Lautens
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Room-temperature alkyl-alkyl Suzuki cross-coupling of alkyl bromides that possess beta hydrogens.

Authors:  M R Netherton; C Dai; K Neuschütz; G C Fu
Journal:  J Am Chem Soc       Date:  2001-10-17       Impact factor: 15.419

10.  Boronic acids: new coupling partners in room-temperature Suzuki reactions of alkyl bromides. Crystallographic characterization of an oxidative-addition adduct generated under remarkably mild conditions.

Authors:  Jan H Kirchhoff; Matthew R Netherton; Ivory D Hills; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2002-11-20       Impact factor: 15.419
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  12 in total

1.  Palladium-catalyzed hydrofunctionalization of vinyl phenol derivatives with heteroaromatics.

Authors:  Tejas P Pathak; Matthew S Sigman
Journal:  Org Lett       Date:  2011-04-21       Impact factor: 6.005

Review 2.  Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors:  Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal:  Chem Rev       Date:  2011-02-14       Impact factor: 60.622

3.  A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents.

Authors:  Tian Qin; Josep Cornella; Chao Li; Lara R Malins; Jacob T Edwards; Shuhei Kawamura; Brad D Maxwell; Martin D Eastgate; Phil S Baran
Journal:  Science       Date:  2016-04-21       Impact factor: 47.728

4.  Pd(II)-catalyzed oxidative 1,1-diarylation of terminal olefins.

Authors:  Erik W Werner; Kaveri B Urkalan; Matthew S Sigman
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

5.  On the mechanism of the palladium-catalyzed tert-butylhydroperoxide-mediated Wacker-type oxidation of alkenes using quinoline-2-oxazoline ligands.

Authors:  Brian W Michel; Laura D Steffens; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2011-05-09       Impact factor: 15.419

6.  Anti-Markovnikov hydroalkylation of allylic amine derivatives via a palladium-catalyzed reductive cross-coupling reaction.

Authors:  Ryan J DeLuca; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2011-07-11       Impact factor: 15.419

7.  Palladium-catalyzed hydroarylation of 1,3-dienes with boronic esters via reductive formation of pi-allyl palladium intermediates under oxidative conditions.

Authors:  Longyan Liao; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2010-08-04       Impact factor: 15.419

8.  Catalyst-controlled Wacker-type oxidation of protected allylic amines.

Authors:  Brian W Michel; Jessica R McCombs; Andrea Winkler; Matthew S Sigman
Journal:  Angew Chem Int Ed Engl       Date:  2010-09-24       Impact factor: 15.336

9.  The palladium-catalyzed anti-Markovnikov hydroalkylation of allylic alcohol derivatives.

Authors:  Ryan J DeLuca; Matthew S Sigman
Journal:  Org Lett       Date:  2012-12-19       Impact factor: 6.005

10.  Palladium-catalyzed allylic cross-coupling reactions of primary and secondary homoallylic electrophiles.

Authors:  Benjamin J Stokes; Susanne M Opra; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2012-07-06       Impact factor: 15.419
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