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Literature DB >> 27104749

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

William B Reid¹, Jesse J Spillane¹, Sarah B Krause¹, Donald A Watson¹.

Abstract

We report the first example of a boryl-Heck reaction using an electrophilic boron reagent. This palladium-catalyzed process allows for the conversion of terminal alkenes to trans-alkenyl boronic esters using commercially available catecholchloroborane (catBCl). In situ transesterification allows for rapid access to a variety of boronic esters, amides, and other alkenyl boron adducts.

Entities: Chemical Disease Gene

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Year: 2016 PMID： 27104749 PMCID： PMC4957246 DOI： 10.1021/jacs.6b02914

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

26 in total

1. Selective C-H borylation of alkenes by palladium pincer complex catalyzed oxidative functionalization.

Authors: Nicklas Selander; Benjamin Willy; Kálmán J Szabó
Journal: Angew Chem Int Ed Engl Date: 2010-06-01 Impact factor: 15.336

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

Authors: Ibraheem A I Mkhalid; 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
Journal: Dalton Trans Date: 2007-12-20 Impact factor: 4.390

3. Preparation of allyl and vinyl silanes by the palladium-catalyzed silylation of terminal olefins: a silyl-Heck reaction.

Authors: Jesse R McAtee; Sara E S Martin; Derek T Ahneman; Keywan A Johnson; Donald A Watson
Journal: Angew Chem Int Ed Engl Date: 2012-03-01 Impact factor: 15.336

4. Efficient synthesis of diborylalkenes from alkenes and diboron by a new PSiP-pincer palladium-catalyzed dehydrogenative borylation.

Authors: Jun Takaya; Naohiro Kirai; Nobuharu Iwasawa
Journal: J Am Chem Soc Date: 2011-08-02 Impact factor: 15.419

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

1. Selective C-H borylation of alkenes by palladium pincer complex catalyzed oxidative functionalization.

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

3. Preparation of allyl and vinyl silanes by the palladium-catalyzed silylation of terminal olefins: a silyl-Heck reaction.

4. Efficient synthesis of diborylalkenes from alkenes and diboron by a new PSiP-pincer palladium-catalyzed dehydrogenative borylation.

5. Palladium-catalyzed carboboration of alkynes using chloroborane and organozirconium reagents.

6. Synthesis of alkenyl boronates from allyl-substituted aromatics using an olefin cross-metathesis protocol.

7. Metal-catalyzed reactions of diborons for synthesis of organoboron compounds.

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

9. Rhodium-catalyzed dehydrogenative borylation of cyclic alkenes.

10. Catalyst-Free Synthesis of Borylated Lactones from Esters via Electrophilic Oxyboration.

Review 1. Cross-Coupling of Heteroatomic Electrophiles.

2. Synthesis of Unsaturated Silyl Heterocycles via an Intramolecular Silyl-Heck Reaction.

Review 3. Inorganometallics (Transition Metal-Metalloid Complexes) and Catalysis.

4. Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction.

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

6. Heck-like Reactions Involving Heteroatomic Electrophiles.

7. Palladium-Catalyzed Cross-Coupling of Silyl Electrophiles with Alkylzinc Halides: A Silyl-Negishi Reaction.

8. A Bench-Stable, Single-Component Precatalyst for Silyl-Heck Reactions.

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

10. C-Boron Enolates Enable Palladium Catalyzed Carboboration of Internal 1,3-Enynes.