Literature DB >> 22946672

Palladium-catalyzed borylation of aryl and heteroaryl halides utilizing tetrakis(dimethylamino)diboron: one step greener.

Gary A Molander1, Sarah L J Trice, Steven M Kennedy.   

Abstract

The palladium-catalyzed borylation of aryl and heteroaryl halides with a novel borylating agent, tetrakis(dimethylamino)diboron [(Me(2)N)(2)B-B(NMe(2))(2)], is reported. The method is complementary to the previously reported method utilizing bis-boronic acid (BBA) in that certain substrates perform better under one set of optimized reaction conditions than the other. Because tetrakis(dimethylamino)diboron is the synthetic precursor to both BBA and bis(pinacolato)diboron (B(2)Pin(2)), the new method represents a more atom-economical and efficient approach to current borylation methods.

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Year:  2012        PMID： 22946672      PMCID： PMC3464102          DOI： 10.1021/ol302124j

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


  23 in total

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4.  Palladium pincer complex catalyzed substitution of vinyl cyclopropanes, vinyl aziridines, and allyl acetates with tetrahydroxydiboron. An efficient route to functionalized allylboronic acids and potassium trifluoro(allyl)borates.

Authors:  Sara Sebelius; Vilhelm J Olsson; Kálmán J Szabó
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5.  Bromo-boronolactonization of olefins.

Authors:  J R Falck; M Bondlela; S K Venkataraman; D Srinivas
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6.  Efficient monophosphorus ligands for palladium-catalyzed Miyaura borylation.

Authors:  Wenjun Tang; Santosh Keshipeddy; Yongda Zhang; Xudong Wei; Jolaine Savoie; Nitinchandra D Patel; Nathan K Yee; Chris H Senanayake
Journal:  Org Lett       Date:  2011-02-14       Impact factor: 6.005

7.  A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids.

Authors:  Tom Kinzel; Yong Zhang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

8.  Palladium-catalyzed, direct boronic acid synthesis from aryl chlorides: a simplified route to diverse boronate ester derivatives.

Authors:  Gary A Molander; Sarah L J Trice; Spencer D Dreher
Journal:  J Am Chem Soc       Date:  2010-11-24       Impact factor: 15.419

9.  Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid.

Authors:  Gary A Molander; Sarah L J Trice; Steven M Kennedy; Spencer D Dreher; Matthew T Tudge
Journal:  J Am Chem Soc       Date:  2012-07-06       Impact factor: 15.419

10.  Petasis Borono-Mannich reaction and allylation of carbonyl compounds via transient allyl boronates generated by palladium-catalyzed substitution of allyl alcohols. an efficient one-pot route to stereodefined alpha-amino acids and homoallyl alcohols.

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Journal:  J Am Chem Soc       Date:  2007-10-12       Impact factor: 15.419
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  5 in total

1.  Scalable, Metal- and Additive-Free, Photoinduced Borylation of Haloarenes and Quaternary Arylammonium Salts.

Authors:  Adelphe M Mfuh; John D Doyle; Bhuwan Chhetri; Hadi D Arman; Oleg V Larionov
Journal:  J Am Chem Soc       Date:  2016-03-01       Impact factor: 15.419

2.  Organoboron chemistry comes to light: recent advances in photoinduced synthetic approaches to organoboron compounds.

Authors:  Viet D Nguyen; Vu T Nguyen; Shengfei Jin; Hang T Dang; Oleg V Larionov
Journal:  Tetrahedron       Date:  2018-12-24       Impact factor: 2.457

3.  Synthesis and Suzuki-Miyaura Cross-Coupling of Enantioenriched Secondary Potassium β-Trifluoroboratoamides: Catalytic, Asymmetric Conjugate Addition of Bisboronic Acid and Tetrakis(dimethylamino)diboron to α,β-Unsaturated Carbonyl Compounds.

Authors:  Gary A Molander; Steven R Wisniewski; Mona Hosseini-Sarvari
Journal:  Adv Synth Catal       Date:  2013-10-11       Impact factor: 5.837

4.  Palladium-catalyzed hydroxylation of aryl and heteroaryl halides enabled by the use of a palladacycle precatalyst.

Authors:  Chi Wai Cheung; Stephen L Buchwald
Journal:  J Org Chem       Date:  2014-05-06       Impact factor: 4.354

5.  Convenient and General Zinc-Catalyzed Borylation of Aryl Diazonium Salts and Aryltriazenes under Mild Conditions.

Authors:  Xinxin Qi; Li-Bing Jiang; Chao Zhou; Jin-Bao Peng; Xiao-Feng Wu
Journal:  ChemistryOpen       Date:  2017-03-16       Impact factor: 2.911
  5 in total

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