Strategic Trimethylsilyldiazomethane Insertion into pinB-SR Followed by Selective Alkylations

Marc G. Civit; Jordi Royes; Christopher M. Vogels; Stephen A. Westcott; Ana B. Cuenca; Elena Fernández

doi:10.1021/acs.orglett.6b01840

Strategic Trimethylsilyldiazomethane Insertion into pinB-SR Followed by Selective Alkylations

Marc G. Civit
, Jordi Royes
, Christopher M. Vogels
, Stephen A. Westcott^*
, Ana B. Cuenca
, Elena Fernández

^*Corresponding author for this work

Research output: Indexed journal article › Article › peer-review

18 Citations (Scopus)

Abstract

The insertion of the diazo derivative Me₃SiCHN₂ into pinB-SR σ bonds (R = Ph, Tol, Bn) allows a direct synthesis of multisubstituted H-C(SR)(Bpin)(SiMe₃) compounds. Consecutive base-assisted transformations of HC(S)(B) (Si) systems lead to deborylative alkylations, Sommelet-Haüser rearrangements, and deprotoalkylations. Intramolecular cyclizations can be selectively performed either via desilylative or deborylative manifolds by fine-tuning the base employed.

Original language	English
Pages (from-to)	3830-3833
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.6b01840
Publication status	Published - 5 Aug 2016
Externally published	Yes

Keywords

Addition-reactions
Boronic esters
Alkyl-halides
Carbanions
Deprotonation
Homologation
Diborylation
Derivatives
Alcohols
Boranes

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10.1021/acs.orglett.6b01840

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@article{69dc1c57e7af4678a85d8e4753570fcf,

title = "Strategic Trimethylsilyldiazomethane Insertion into pinB-SR Followed by Selective Alkylations",

abstract = "The insertion of the diazo derivative Me3SiCHN2 into pinB-SR σ bonds (R = Ph, Tol, Bn) allows a direct synthesis of multisubstituted H-C(SR)(Bpin)(SiMe3) compounds. Consecutive base-assisted transformations of HC(S)(B) (Si) systems lead to deborylative alkylations, Sommelet-Ha{\"u}ser rearrangements, and deprotoalkylations. Intramolecular cyclizations can be selectively performed either via desilylative or deborylative manifolds by fine-tuning the base employed.",

keywords = "Addition-reactions, Boronic esters, Alkyl-halides, Carbanions, Deprotonation, Homologation, Diborylation, Derivatives, Alcohols, Boranes",

author = "Civit, \{Marc G.\} and Jordi Royes and Vogels, \{Christopher M.\} and Westcott, \{Stephen A.\} and Cuenca, \{Ana B.\} and Elena Fern{\'a}ndez",

note = "Funding Information: The present research was supported by the Spanish Ministerio de Economia y Competitividad (MINECO) through Project No. CTQ2013-43395P (EF) and by NSERC (SAW) Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

month = aug,

day = "5",

doi = "10.1021/acs.orglett.6b01840",

language = "English",

volume = "18",

pages = "3830--3833",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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T1 - Strategic Trimethylsilyldiazomethane Insertion into pinB-SR Followed by Selective Alkylations

AU - Civit, Marc G.

AU - Royes, Jordi

AU - Vogels, Christopher M.

AU - Westcott, Stephen A.

AU - Cuenca, Ana B.

AU - Fernández, Elena

N1 - Funding Information: The present research was supported by the Spanish Ministerio de Economia y Competitividad (MINECO) through Project No. CTQ2013-43395P (EF) and by NSERC (SAW) Publisher Copyright: © 2016 American Chemical Society.

PY - 2016/8/5

Y1 - 2016/8/5

N2 - The insertion of the diazo derivative Me3SiCHN2 into pinB-SR σ bonds (R = Ph, Tol, Bn) allows a direct synthesis of multisubstituted H-C(SR)(Bpin)(SiMe3) compounds. Consecutive base-assisted transformations of HC(S)(B) (Si) systems lead to deborylative alkylations, Sommelet-Haüser rearrangements, and deprotoalkylations. Intramolecular cyclizations can be selectively performed either via desilylative or deborylative manifolds by fine-tuning the base employed.

AB - The insertion of the diazo derivative Me3SiCHN2 into pinB-SR σ bonds (R = Ph, Tol, Bn) allows a direct synthesis of multisubstituted H-C(SR)(Bpin)(SiMe3) compounds. Consecutive base-assisted transformations of HC(S)(B) (Si) systems lead to deborylative alkylations, Sommelet-Haüser rearrangements, and deprotoalkylations. Intramolecular cyclizations can be selectively performed either via desilylative or deborylative manifolds by fine-tuning the base employed.

KW - Addition-reactions

KW - Boronic esters

KW - Alkyl-halides

KW - Carbanions

KW - Deprotonation

KW - Homologation

KW - Diborylation

KW - Derivatives

KW - Alcohols

KW - Boranes

UR - https://www.scopus.com/pages/publications/84981201008

UR - https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=pure_univeritat_ramon_llull&SrcAuth=WosAPI&KeyUT=WOS:000381236300081&DestLinkType=FullRecord&DestApp=WOS_CPL

U2 - 10.1021/acs.orglett.6b01840

DO - 10.1021/acs.orglett.6b01840

M3 - Article

C2 - 27456039

AN - SCOPUS:84981201008

SN - 1523-7060

VL - 18

SP - 3830

EP - 3833

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Strategic Trimethylsilyldiazomethane Insertion into pinB-SR Followed by Selective Alkylations

Abstract

Keywords

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