Rhodium(I)-Catalyzed Synthesis of Indoles: Amino-Claisen Rearrangement of N-Propargylanilines
Akio Saito; Shoko Oda; Haruhiko Fukaya; Yuji Hanzawa; Journal of Organic Chemistry 74 (2009) 1517–1524; doi:10.1021/jo8022523

data_4024324
_publ_contact_author_address
;
 Laboratory of Organic Reaction Chemistry, Showa Pharmaceutical
University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo 194-8543, Japan
;
_publ_contact_author_email       akio-sai@ac.shoyaku.ac.jp
_publ_contact_author_name        'Akio Saito '
_publ_section_title
;
Rhodium(I)-Catalyzed Synthesis of Indoles: Amino-Claisen Rearrangement
of N-Propargylanilines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1517
_journal_page_last               1524
_journal_paper_doi               10.1021/jo8022523
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C40 H31 F6 O2 P2 Rh'
_chemical_formula_sum            'C40 H31 F6 O2 P2 Rh'
_chemical_formula_weight         822.50
_chemical_name_systematic
; 
carbonyl(1,1,1,
3,3,3-hexafluoropropan-2-olato-kO)bis(triphenylphosphane)rhodium(I)
 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             '28 July 08'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.179(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.973(6)
_cell_length_b                   12.492(3)
_cell_length_c                   29.095(8)
_cell_measurement_reflns_used    9828
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.30
_cell_volume                     7166(3)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'multilayer confocal mirror'
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            81007
_diffrn_reflns_theta_full        27.65
_diffrn_reflns_theta_max         27.65
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  0.9337
_exptl_absorpt_correction_T_min  0.9111
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3328
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.948
_refine_diff_density_min         -0.713
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     974
_refine_ls_number_reflns         16555
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0327
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0265P)^2^+6.1334P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0798
_reflns_number_gt                13829
_reflns_number_total             16555
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8022523_si_002.cif
_cod_data_source_block           rh-hfip
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4024324