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Development of nickel-catalyzed asym...

Cherney, Alan Hayden.

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Development of nickel-catalyzed asymmetric reductive cross-coupling of benzylic electrophiles.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Development of nickel-catalyzed asymmetric reductive cross-coupling of benzylic electrophiles./
Author:	Cherney, Alan Hayden.
Description:	472 p.
Notes:	Source: Dissertation Abstracts International, Volume: 76-10(E), Section: B.
Contained By:	Dissertation Abstracts International76-10B(E).
Subject:	Organic chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3706453
ISBN:	9781321802931

Development of nickel-catalyzed asymmetric reductive cross-coupling of benzylic electrophiles.
Cherney, Alan Hayden.

Development of nickel-catalyzed asymmetric reductive cross-coupling of benzylic electrophiles. - 472 p.

Source: Dissertation Abstracts International, Volume: 76-10(E), Section: B.

Thesis (Ph.D.)--California Institute of Technology, 2015.

Over the last forty years, the advent of transition metal-catalyzed cross-coupling has revolutionized the synthetic chemist's ability to generate C--C bonds. Since the 1970s, a parallel effort to control the stereochemical outcome of such transformations has yielded a variety of chiral catalyst complexes that deliver enantioenriched cross-coupled products. Nonetheless, challenges in the use of C(sp3)-hybridized coupling partners have limited asymmetric variants to a narrow fraction of the total number of cross-coupling methodologies published each year.

ISBN: 9781321802931Subjects--Topical Terms:

523952
Organic chemistry.

Development of nickel-catalyzed asymmetric reductive cross-coupling of benzylic electrophiles.
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020 $a 9781321802931
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100 1 $a Cherney, Alan Hayden. $3 3182554
245 1 0 $a Development of nickel-catalyzed asymmetric reductive cross-coupling of benzylic electrophiles.
300 $a 472 p.
500 $a Source: Dissertation Abstracts International, Volume: 76-10(E), Section: B.
500 $a Adviser: Sarah E. Reisman.
502 $a Thesis (Ph.D.)--California Institute of Technology, 2015.
520 $a Over the last forty years, the advent of transition metal-catalyzed cross-coupling has revolutionized the synthetic chemist's ability to generate C--C bonds. Since the 1970s, a parallel effort to control the stereochemical outcome of such transformations has yielded a variety of chiral catalyst complexes that deliver enantioenriched cross-coupled products. Nonetheless, challenges in the use of C(sp3)-hybridized coupling partners have limited asymmetric variants to a narrow fraction of the total number of cross-coupling methodologies published each year.
520 $a Herein, we report studies on the asymmetric cross-coupling of benzylic groups under either Pd or Ni catalysis. We have developed a Pd-catalyzed Fukuyama cross- coupling of thioesters and secondary benzylzinc halides to deliver racemic ketones under mild conditions. Investigations with chiral catalysts revealed that a promising asymmetric transformation could be achieved to give modestly enantioenriched ketones.
520 $a Reductive cross-coupling, involving the union of two different electrophiles, has the added advantage of avoiding harsh or expensive organometallic reagents. We have discovered the first highly enantioselective Ni-catalyzed reductive cross-couplings of two organohalide electrophiles. Treatment of an acid chloride and a secondary benzyl chloride with a chiral nickel/bis(oxazoline) complex and Mn0 as the stoichiometric reductant furnishes ketone products in good yield and high enantioselectivity. Expanding on this result, we have demonstrated that vinyl bromides and secondary benzyl chlorides can be cross-coupled using a different chiral nickel/bis(oxazoline) complex, illustrating the generality of an asymmetric reductive coupling platform. Preliminary studies directed toward other coupling partners are also disclosed.
590 $a School code: 0037.
650 4 $a Organic chemistry. $3 523952
650 4 $a Chemistry. $3 516420
690 $a 0490
690 $a 0485
710 2 $a California Institute of Technology. $b Chemistry. $3 2096080
773 0 $t Dissertation Abstracts International $g 76-10B(E).
790 $a 0037
791 $a Ph.D.
792 $a 2015
793 $a English
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3706453