Literature DB >> 30350673

Synthesis of Trisubstituted Alkenyl Boronic Esters from Alkenes Using the Boryl-Heck Reaction.

William B Reid1, Donald A Watson1.   

Abstract

The direct borylation of disubstituted alkenes is reported. These conditions allow for the conversion of a variety 1,1- and 1,2-disubstituted alkenes to trisubstituted alkenyl boronic esters with outstanding yields and excellent E/ Z selectivities. The utility of this reaction has been demonstrated with several downstream functionalization reactions, which allow access to diverse, stereodefined, functionalized olefins. Mechanistic studies are consistent with a boryl-Heck pathway.

Entities:  

Year:  2018        PMID： 30350673      PMCID： PMC6388719          DOI： 10.1021/acs.orglett.8b02949

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


  19 in total

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4.  Application of hitherto unexplored macrocyclization strategies in the epothilone series: novel epothilone analogs by total synthesis.

Authors:  Jon T Njardarson; Kaustav Biswas; Samuel J Danishefsky
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5.  Palladium-catalyzed cross-coupling reactions in total synthesis.

Authors:  K C Nicolaou; Paul G Bulger; David Sarlah
Journal:  Angew Chem Int Ed Engl       Date:  2005-07-18       Impact factor: 15.336

6.  Enantioselective Heck arylations of acyclic alkenyl alcohols using a redox-relay strategy.

Authors:  Erik W Werner; Tian-Sheng Mei; Alexander J Burckle; Matthew S Sigman
Journal:  Science       Date:  2012-12-14       Impact factor: 47.728

7.  Enantioselective Palladium-Catalyzed Alkenylation of Trisubstituted Alkenols To Form Allylic Quaternary Centers.

Authors:  Harshkumar H Patel; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2016-10-25       Impact factor: 15.419

8.  Rhodium catalysed dehydrogenative borylation of vinylarenes and 1,1-disubstituted alkenes without sacrificial hydrogenation--a route to 1,1-disubstituted vinylboronates.

Authors:  R Benjamin Coapes; Fabio E S Souza; Rhodri Ll Thomas; Jonathan J Hall; Todd B Marder
Journal:  Chem Commun (Camb)       Date:  2003-03-07       Impact factor: 6.222

9.  Copper-promoted coupling of vinyl boronates and alcohols: a mild synthesis of allyl vinyl ethers.

Authors:  Ryan E Shade; Alan M Hyde; John-Carl Olsen; Craig A Merlic
Journal:  J Am Chem Soc       Date:  2010-02-03       Impact factor: 15.419

10.  Rational design of a second generation catalyst for preparation of allylsilanes using the silyl-Heck reaction.

Authors:  Jesse R McAtee; Glenn P A Yap; Donald A Watson
Journal:  J Am Chem Soc       Date:  2014-07-08       Impact factor: 15.419
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  6 in total

Review 1.  Cross-Coupling of Heteroatomic Electrophiles.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

2.  Olefin Functionalization/Isomerization Enables Stereoselective Alkene Synthesis.

Authors:  Chen-Fei Liu; Hongyu Wang; Robert T Martin; Haonan Zhao; Osvaldo Gutierrez; Ming Joo Koh
Journal:  Nat Catal       Date:  2021-07-29

3.  Visible Light-Induced Pd-Catalyzed Alkyl-Heck Reaction of Oximes.

Authors:  Nikita Kvasovs; Valeriia Iziumchenko; Vitalii Palchykov; Vladimir Gevorgyan
Journal:  ACS Catal       Date:  2021-03-09       Impact factor: 13.084

Review 4.  Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm.

Authors:  Christopher S Horbaczewskyj; Ian J S Fairlamb
Journal:  Org Process Res Dev       Date:  2022-07-11       Impact factor: 3.858

5.  Synthesis of 1,1-Diboryl Alkenes Using the Boryl-Heck Reaction.

Authors:  Olamide O Idowu; Jacob C Hayes; William B Reid; Donald A Watson
Journal:  Org Lett       Date:  2021-05-27       Impact factor: 6.072

6.  Regio- and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles.

Authors:  Junting Chen; Jiakun Li; Matthew B Plutschack; Florian Berger; Tobias Ritter
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-03       Impact factor: 15.336
  6 in total

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