Literature DB >> 18274686

Rhodium catalysed dehydrogenative borylation of alkenes: vinylboronates via C-H activation.

Ibraheem A I Mkhalid1, R Benjamin Coapes, S Natasha Edes, David N Coventry, Fabio E S Souza, Rhodri Ll Thomas, Jonathan J Hall, Si-Wei Bi, Zhenyang Lin, Todd B Marder.   

Abstract

We present herein a high yield, highly selective catalytic synthesis of vinylboronate esters (VBEs), including 1,1-disubstituted VBEs, from alkenes without significant hydrogenation or hydroboration, using the simple catalyst precursor, trans-[RhCl(CO)(PPh3)2] (1), and the diboron reagents B2pin2 (2a, pin = pinacolato = OCMe2CMe2O) or B2neop2 (2b, neop = neopentylglycolato = OCH2CMe2CH2O), or the monoboron reagent HBpin, all of which are commercially available. The reactions were conducted at 80 degrees C using conventional heating, or in a microwave reactor at 150 degrees C.

Entities:  

Year:  2007        PMID: 18274686     DOI: 10.1039/b715584k

Source DB:  PubMed          Journal:  Dalton Trans        ISSN: 1477-9226            Impact factor:   4.390


  13 in total

1.  Cobalt-Catalyzed 1,1-Diboration of Terminal Alkynes: Scope, Mechanism, and Synthetic Applications.

Authors:  Simon Krautwald; Máté J Bezdek; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2017-03-01       Impact factor: 15.419

2.  Direct Synthesis of Alkenyl Boronic Esters from Unfunctionalized Alkenes: A Boryl-Heck Reaction.

Authors:  William B Reid; Jesse J Spillane; Sarah B Krause; Donald A Watson
Journal:  J Am Chem Soc       Date:  2016-04-22       Impact factor: 15.419

3.  Synthesis of Stereodefined 1,1-Diborylalkenes via Copper-Catalyzed Diboration of Terminal Alkynes.

Authors:  Yang Gao; Zhong-Qian Wu; Keary M Engle
Journal:  Org Lett       Date:  2020-06-23       Impact factor: 6.005

Review 4.  Inorganometallics (Transition Metal-Metalloid Complexes) and Catalysis.

Authors:  Bogdan Marciniec; Cezary Pietraszuk; Piotr Pawluć; Hieronim Maciejewski
Journal:  Chem Rev       Date:  2021-12-30       Impact factor: 60.622

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

Authors:  William B Reid; Donald A Watson
Journal:  Org Lett       Date:  2018-10-16       Impact factor: 6.005

6.  Rhodium-catalyzed dehydrogenative borylation of cyclic alkenes.

Authors:  Azusa Kondoh; Timothy F Jamison
Journal:  Chem Commun (Camb)       Date:  2010-01-05       Impact factor: 6.222

7.  Ortho-aryl substituted DPEphos ligands: rhodium complexes featuring C-H anagostic interactions and B-H agostic bonds.

Authors:  James J Race; Arron L Burnage; Timothy M Boyd; Alex Heyam; Antonio J Martínez-Martínez; Stuart A Macgregor; Andrew S Weller
Journal:  Chem Sci       Date:  2021-05-25       Impact factor: 9.825

8.  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

9.  Convenient methods for preparing pi-conjugated linkers as building blocks for modular chemistry.

Authors:  Jirí Kulhánek; Filip Bures; Miroslav Ludwig
Journal:  Beilstein J Org Chem       Date:  2009-04-14       Impact factor: 2.883

10.  Mechanistic Insights into Carbonyl-Directed Rhodium-Catalyzed Hydroboration: ab Initio Study of a Cyclic γ,δ-Unsaturated Amide.

Authors:  Zhao-Di Yang; Rhitankar Pal; Gia L Hoang; Xiao Cheng Zeng; James M Takacs
Journal:  ACS Catal       Date:  2014-01-22       Impact factor: 13.084

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