The Catalyst-Controlled Regiodivergent Chlorination of Phenols

Sean M. Maddox; Andrew N. Dinh; Felipe Armenta; Joann Um; Jeffrey L. Gustafson

doi:10.1021/acs.orglett.6b02650

The Catalyst-Controlled Regiodivergent Chlorination of Phenols

Sean M. Maddox
, Andrew N. Dinh
, Felipe Armenta
, Joann Um
, Jeffrey L. Gustafson

Chemistry

San Diego State University
Southwestern College

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

64 Scopus citations

Abstract

Different catalysts are demonstrated to overcome or augment a substrate's innate regioselectivity. Nagasawa's bis-thiourea catalyst was found to overcome the innate para-selectivity of electrophilic phenol chlorination, yielding ortho-chlorinated phenols that are not readily obtainable via canonical electrophilic chlorinations. Conversely, a phosphine sulfide derived from 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) was found to enhance the innate para-preference of phenol chlorination.

Original language	English
Pages (from-to)	5476-5479
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.6b02650
State	Published - Nov 4 2016

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title = "The Catalyst-Controlled Regiodivergent Chlorination of Phenols",

abstract = "Different catalysts are demonstrated to overcome or augment a substrate's innate regioselectivity. Nagasawa's bis-thiourea catalyst was found to overcome the innate para-selectivity of electrophilic phenol chlorination, yielding ortho-chlorinated phenols that are not readily obtainable via canonical electrophilic chlorinations. Conversely, a phosphine sulfide derived from 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) was found to enhance the innate para-preference of phenol chlorination.",

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AU - Maddox, Sean M.

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AU - Um, Joann

AU - Gustafson, Jeffrey L.

PY - 2016/11/4

Y1 - 2016/11/4

N2 - Different catalysts are demonstrated to overcome or augment a substrate's innate regioselectivity. Nagasawa's bis-thiourea catalyst was found to overcome the innate para-selectivity of electrophilic phenol chlorination, yielding ortho-chlorinated phenols that are not readily obtainable via canonical electrophilic chlorinations. Conversely, a phosphine sulfide derived from 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) was found to enhance the innate para-preference of phenol chlorination.

AB - Different catalysts are demonstrated to overcome or augment a substrate's innate regioselectivity. Nagasawa's bis-thiourea catalyst was found to overcome the innate para-selectivity of electrophilic phenol chlorination, yielding ortho-chlorinated phenols that are not readily obtainable via canonical electrophilic chlorinations. Conversely, a phosphine sulfide derived from 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) was found to enhance the innate para-preference of phenol chlorination.

UR - https://www.scopus.com/pages/publications/84994632107

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ER -

The Catalyst-Controlled Regiodivergent Chlorination of Phenols

Abstract

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