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Related Concept Videos

Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene01:17

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
Halogenation of Alkenes02:46

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...

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Related Experiment Video

Updated: May 21, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

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Outer-sphere direction in iridium C-H borylation.

Philipp C Roosen1, Venkata A Kallepalli, Buddhadeb Chattopadhyay

  • 1Department of Chemistry, Michigan State University, East Lansing, Michigan 48824-1322, USA.

Journal of the American Chemical Society
|June 19, 2012
PubMed
Summary
This summary is machine-generated.

The NHBoc group enables selective C-H borylations in arenes and alkenes. This outer sphere mechanism involves hydrogen bonding, offering unique regioselectivities complementary to directed ortho metalations.

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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Area of Science:

  • Organic Chemistry
  • Catalysis

Background:

  • Directed ortho metalations are common for functionalizing aromatic rings.
  • C-H borylation is a powerful tool for introducing boron functional groups.
  • Developing new methods for regioselective C-H functionalization is crucial.

Purpose of the Study:

  • To introduce the NHBoc group for ortho selective C-H borylations.
  • To elucidate the mechanism of this novel borylation reaction.
  • To compare the regioselectivity with existing methods like directed ortho metalations.

Main Methods:

  • Experimental studies involving arenes and alkenes.
  • Computational investigations to understand reaction mechanisms.
  • Analysis of regioselectivity in C-H borylation reactions.

Main Results:

  • The NHBoc group successfully directed ortho selective C-H borylations.
  • An outer sphere mechanism was proposed and supported by data.
  • The N-H proton's hydrogen bonding to a boryl ligand oxygen was identified as key.
  • Unique regioselectivities were observed, distinct from directed ortho metalations.

Conclusions:

  • The NHBoc group is an effective directing group for regioselective C-H borylation.
  • The outer sphere mechanism provides new mechanistic insights into C-H functionalization.
  • This method offers complementary regioselectivity to established ortho functionalization techniques.