Literature DB >> 19594167

sp2-sp3 hybridized mixed diboron: synthesis, characterization, and copper-catalyzed beta-boration of alpha,beta-unsaturated conjugated compounds.

Ming Gao1, Steven B Thorpe, Webster L Santos.   

Abstract

A novel sp(2)-sp(3) hybridized mixed diboron and its reactivity on the copper-catalyzed beta-boration of alpha,beta-unsaturated conjugated compounds to afford the corresponding beta-borated compounds is reported. The presence of sp(3)-hybridized boron provides a mild beta-boration condition in the absence of phosphine and base additives. Finally, our investigations demonstrate that the sp(2)-hybridized boron of the mixed diboron is selectively transferred to the beta-carbon of conjugated substrates.

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Year:  2009        PMID: 19594167     DOI: 10.1021/ol901359n

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


  10 in total

1.  A method for the deprotection of alkylpinacolyl boronate esters.

Authors:  Jing Sun; Michael T Perfetti; Webster L Santos
Journal:  J Org Chem       Date:  2011-04-07       Impact factor: 4.354

2.  Enantioselective preparation and chemoselective cross-coupling of 1,1-diboron compounds.

Authors:  Jack Chang Hung Lee; Robert McDonald; Dennis G Hall
Journal:  Nat Chem       Date:  2011-09-25       Impact factor: 24.427

3.  Bioorthogonal Click and Release: A General, Rapid, Chemically Revertible Bioconjugation Strategy Employing Enamine N-oxides.

Authors:  Dahye Kang; Sanghyeon Lee; Justin Kim
Journal:  Chem       Date:  2022-06-15       Impact factor: 25.832

4.  Kinetic and Spectroscopic Studies of Aerobic Copper(II)-Catalyzed Methoxylation of Arylboronic Esters and Insights into Aryl Transmetalation to Copper(II).

Authors:  Amanda E King; Bradford L Ryland; Thomas C Brunold; Shannon S Stahl
Journal:  Organometallics       Date:  2012-08-24       Impact factor: 3.876

5.  Copper(II)-catalyzed silylation of activated alkynes in water: diastereodivergent access to E- or Z-β-silyl-α,β-unsaturated carbonyl and carboxyl compounds.

Authors:  Joseph A Calderone; Webster L Santos
Journal:  Angew Chem Int Ed Engl       Date:  2014-02-14       Impact factor: 15.336

6.  Enantioselective Rhodium(III)-Catalyzed Markovnikov Hydroboration of Unactivated Terminal Alkenes.

Authors:  James R Smith; Beatrice S L Collins; Matthew J Hesse; Mark A Graham; Eddie L Myers; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2017-06-30       Impact factor: 15.419

7.  Regio- and Stereoselective Synthesis of 1,1-Diborylalkenes via Brønsted Base-Catalyzed Mixed Diboration of Alkynyl Esters and Amides with BpinBdan.

Authors:  Xiaocui Liu; Wenbo Ming; Xiaoling Luo; Alexandra Friedrich; Jan Maier; Udo Radius; Webster L Santos; Todd B Marder
Journal:  European J Org Chem       Date:  2020-03-18

8.  Palladium-catalyzed hydroboration reaction of unactivated alkynes with bis (pinacolato) diboron in water.

Authors:  Ming Yang; Yunzi Yu; Wenxia Ma; Yuqin Feng; Gang Zhang; Yaqi Wu; Fanyu Zhou; Yongsheng Yang; Dezheng Liu
Journal:  RSC Adv       Date:  2022-03-29       Impact factor: 3.361

9.  Facile scission of isonitrile carbon-nitrogen triple bond using a diborane(4) reagent.

Authors:  Hiroki Asakawa; Ka-Ho Lee; Zhenyang Lin; Makoto Yamashita
Journal:  Nat Commun       Date:  2014-06-26       Impact factor: 14.919

10.  Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions.

Authors:  Kai Chen; Shuai Zhang; Pei He; Pengfei Li
Journal:  Chem Sci       Date:  2016-02-01       Impact factor: 9.825

  10 in total

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