Cyclization strategies to polyenes using Pd(II)-catalyzed couplings of pinacol vinylboronates

Robert G. Iafe; Daniel G. Chan; Jonathan L. Kuo; Byron A. Boon; Darius J. Faizi; Tomomi Saga; Jonathan W. Turner; Craig A. Merlic

doi:10.1021/ol3020623

Cyclization strategies to polyenes using Pd(II)-catalyzed couplings of pinacol vinylboronates

Robert G. Iafe
, Daniel G. Chan
, Jonathan L. Kuo
, Byron A. Boon
, Darius J. Faizi
, Tomomi Saga
, Jonathan W. Turner
, Craig A. Merlic

Chemistry

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

As a complement to Pd(0)-catalyzed cyclizations, seven Pd(II)-catalyzed cyclization strategies are reported. α,ω-Diynes are selectively hydroborated to bis(boronate esters), which cyclize under Pd(II)-catalysis producing a diverse array of small, medium, and macrocyclic polyenes with controlled E,E, Z,Z, or E,Z stereochemistry. Various functional groups are tolerated including aryl bromides, and applications are illustrated.

Original language	English (US)
Pages (from-to)	4282-4285
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	16
DOIs	https://doi.org/10.1021/ol3020623
State	Published - Aug 17 2012

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol3020623

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title = "Cyclization strategies to polyenes using Pd(II)-catalyzed couplings of pinacol vinylboronates",

abstract = "As a complement to Pd(0)-catalyzed cyclizations, seven Pd(II)-catalyzed cyclization strategies are reported. α,ω-Diynes are selectively hydroborated to bis(boronate esters), which cyclize under Pd(II)-catalysis producing a diverse array of small, medium, and macrocyclic polyenes with controlled E,E, Z,Z, or E,Z stereochemistry. Various functional groups are tolerated including aryl bromides, and applications are illustrated.",

author = "Iafe, \{Robert G.\} and Chan, \{Daniel G.\} and Kuo, \{Jonathan L.\} and Boon, \{Byron A.\} and Faizi, \{Darius J.\} and Tomomi Saga and Turner, \{Jonathan W.\} and Merlic, \{Craig A.\}",

year = "2012",

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doi = "10.1021/ol3020623",

language = "English (US)",

volume = "14",

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journal = "Organic Letters",

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TY - JOUR

T1 - Cyclization strategies to polyenes using Pd(II)-catalyzed couplings of pinacol vinylboronates

AU - Iafe, Robert G.

AU - Chan, Daniel G.

AU - Kuo, Jonathan L.

AU - Boon, Byron A.

AU - Faizi, Darius J.

AU - Saga, Tomomi

AU - Turner, Jonathan W.

AU - Merlic, Craig A.

PY - 2012/8/17

Y1 - 2012/8/17

N2 - As a complement to Pd(0)-catalyzed cyclizations, seven Pd(II)-catalyzed cyclization strategies are reported. α,ω-Diynes are selectively hydroborated to bis(boronate esters), which cyclize under Pd(II)-catalysis producing a diverse array of small, medium, and macrocyclic polyenes with controlled E,E, Z,Z, or E,Z stereochemistry. Various functional groups are tolerated including aryl bromides, and applications are illustrated.

AB - As a complement to Pd(0)-catalyzed cyclizations, seven Pd(II)-catalyzed cyclization strategies are reported. α,ω-Diynes are selectively hydroborated to bis(boronate esters), which cyclize under Pd(II)-catalysis producing a diverse array of small, medium, and macrocyclic polyenes with controlled E,E, Z,Z, or E,Z stereochemistry. Various functional groups are tolerated including aryl bromides, and applications are illustrated.

UR - https://www.scopus.com/pages/publications/84865250456

UR - https://www.scopus.com/pages/publications/84865250456#tab=citedBy

U2 - 10.1021/ol3020623

DO - 10.1021/ol3020623

M3 - Article

C2 - 22867013

AN - SCOPUS:84865250456

SN - 1523-7060

VL - 14

SP - 4282

EP - 4285

JO - Organic Letters

JF - Organic Letters

IS - 16

ER -

Cyclization strategies to polyenes using Pd(II)-catalyzed couplings of pinacol vinylboronates

Abstract

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