Abstract
Cross-coupling reactions are a staple in organic synthesis, especially for C-C bond formation with sp- and sp2-carbon electrophiles. In recent years, the range of accessible C-C bonds has been extended to stereogenic centers which expedites access to greater molecular complexity. However, these reactions predominantly depend upon late transition metal (LTM) catalysts whose cost, toxicity, and/or environmental impact have come under increasing scrutiny and governmental regulation. Here, we report Mn(II)Cl2 complexes alone, or with assistance from copper, catalyze the stereospecific cross-coupling of α-alkoxyalkylstannanes with organic electrophiles with complete retention of configuration.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 1241-1251 |
| Number of pages | 11 |
| Journal | Journal of Organic Chemistry |
| Volume | 83 |
| Issue number | 3 |
| DOIs | |
| State | Published - Feb 2 2018 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Stereospecific Stille Cross-Couplings Using Mn(II)Cl2 . / Dakarapu, Rambabu; Falck, J R.
In: Journal of Organic Chemistry, Vol. 83, No. 3, 02.02.2018, p. 1241-1251.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Stereospecific Stille Cross-Couplings Using Mn(II)Cl2
AU - Dakarapu, Rambabu
AU - Falck, J R
PY - 2018/2/2
Y1 - 2018/2/2
N2 - Cross-coupling reactions are a staple in organic synthesis, especially for C-C bond formation with sp- and sp2-carbon electrophiles. In recent years, the range of accessible C-C bonds has been extended to stereogenic centers which expedites access to greater molecular complexity. However, these reactions predominantly depend upon late transition metal (LTM) catalysts whose cost, toxicity, and/or environmental impact have come under increasing scrutiny and governmental regulation. Here, we report Mn(II)Cl2 complexes alone, or with assistance from copper, catalyze the stereospecific cross-coupling of α-alkoxyalkylstannanes with organic electrophiles with complete retention of configuration.
AB - Cross-coupling reactions are a staple in organic synthesis, especially for C-C bond formation with sp- and sp2-carbon electrophiles. In recent years, the range of accessible C-C bonds has been extended to stereogenic centers which expedites access to greater molecular complexity. However, these reactions predominantly depend upon late transition metal (LTM) catalysts whose cost, toxicity, and/or environmental impact have come under increasing scrutiny and governmental regulation. Here, we report Mn(II)Cl2 complexes alone, or with assistance from copper, catalyze the stereospecific cross-coupling of α-alkoxyalkylstannanes with organic electrophiles with complete retention of configuration.
UR - http://www.scopus.com/inward/record.url?scp=85041585317&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85041585317&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.7b02780
DO - 10.1021/acs.joc.7b02780
M3 - Article
C2 - 29320181
AN - SCOPUS:85041585317
VL - 83
SP - 1241
EP - 1251
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 3
ER -